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<article article-type="research-article" dtd-version="1.3" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xml:lang="en"><front><journal-meta><journal-id journal-id-type="publisher-id">najo</journal-id><journal-title-group><journal-title xml:lang="en">Nanosystems: Physics, Chemistry, Mathematics</journal-title><trans-title-group xml:lang="ru"><trans-title>Наносистемы: физика, химия, математика</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">2220-8054</issn><issn pub-type="epub">2305-7971</issn><publisher><publisher-name>Университет ИТМО</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.17586/2220-8054-2025-16-1-116-122</article-id><article-id custom-type="elpub" pub-id-type="custom">najo-97</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="en"><subject>CHEMISTRY AND MATERIALS SCIENCE</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>ХИМИЯ И НАУКА О МАТЕРИАЛАХ</subject></subj-group></article-categories><title-group><article-title>Synthesis, structure and noncovalent interactions of mesityl(phenyl)phosphine oxide glycolate based hydrogen-bonded nanosized organic framework</article-title><trans-title-group xml:lang="ru"><trans-title>Синтез, структура и нековалентные взаимодействия наноразмерного водородно-связанного каркасного полимера на основе гликолята мезитил(фенил)фосфиноксида</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-5603-1311</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Кагилев</surname><given-names>А. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Kagilev</surname><given-names>A. A.</given-names></name></name-alternatives><bio xml:lang="en"><p>Alexey A. Kagilev</p><p>420088, Kazan</p></bio><email xlink:type="simple">al-kagilev@mail.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-7440-1486</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Сахапов</surname><given-names>И. Ф.</given-names></name><name name-style="western" xml:lang="en"><surname>Sakhapov</surname><given-names>I. F.</given-names></name></name-alternatives><bio xml:lang="en"><p>Ilyas F. Sakhapov</p><p>420088, Kazan</p></bio><email xlink:type="simple">ilyas.sakhapov@iopc.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0001-6615-8968</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Гафуров</surname><given-names>З. Н.</given-names></name><name name-style="western" xml:lang="en"><surname>Gafurov</surname><given-names>Z. N.</given-names></name></name-alternatives><bio xml:lang="en"><p>Zufar N. Gafurov</p><p>420088, Kazan</p></bio><email xlink:type="simple">gafurov.zufar@iopc.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-2285-300X</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Кантюков</surname><given-names>А. О.</given-names></name><name name-style="western" xml:lang="en"><surname>Kantyukov</surname><given-names>A. O.</given-names></name></name-alternatives><bio xml:lang="en"><p>Artyom O. Kantyukov</p><p>420088, Kazan</p></bio><email xlink:type="simple">kant.art@mail.ru</email><xref ref-type="aff" rid="aff-2"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0001-9373-2996</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Михайлов</surname><given-names>И. К.</given-names></name><name name-style="western" xml:lang="en"><surname>Mikhailov</surname><given-names>I. K.</given-names></name></name-alternatives><bio xml:lang="en"><p>Ilya K. Mikhailov</p><p>420088, Kazan</p></bio><email xlink:type="simple">tiimhailovilya@gmail.com</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-5988-1012</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Исламов</surname><given-names>Д. Р.</given-names></name><name name-style="western" xml:lang="en"><surname>Islamov</surname><given-names>D. R.</given-names></name></name-alternatives><bio xml:lang="en"><p>Daut R. Islamov</p><p>420111, Kazan</p></bio><email xlink:type="simple">daut1989@mail.ru</email><xref ref-type="aff" rid="aff-3"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0003-4213-9724</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Герасимов</surname><given-names>А. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Gerasimov</surname><given-names>A. V.</given-names></name></name-alternatives><bio xml:lang="en"><p>Alexander V. Gerasimov</p><p>420008, Kazan</p></bio><email xlink:type="simple">Alexander.Gerasimov@kpfu.ru</email><xref ref-type="aff" rid="aff-4"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-7963-2806</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Филиппов</surname><given-names>О. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Filippov</surname><given-names>O. A.</given-names></name></name-alternatives><bio xml:lang="en"><p>Oleg A. Filippov</p><p>119991, Moscow</p></bio><email xlink:type="simple">h-bond@ineos.ac.ru</email><xref ref-type="aff" rid="aff-5"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-8114-7025</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Губайдуллин</surname><given-names>А. Т.</given-names></name><name name-style="western" xml:lang="en"><surname>Gubaidullin</surname><given-names>A. T.</given-names></name></name-alternatives><bio xml:lang="en"><p>Aidar T. Gubaidullin</p><p>420088, Kazan</p></bio><email xlink:type="simple">aidar@iopc.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0003-3107-5251</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Софичева</surname><given-names>О. С.</given-names></name><name name-style="western" xml:lang="en"><surname>Soficheva</surname><given-names>O. S.</given-names></name></name-alternatives><bio xml:lang="en"><p>Olga S. Soficheva</p><p>420088, Kazan</p></bio><email xlink:type="simple">myaolechka@yandex.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-2241-9764</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Синяшин</surname><given-names>О. Г.</given-names></name><name name-style="western" xml:lang="en"><surname>Sinyashin</surname><given-names>O. G.</given-names></name></name-alternatives><bio xml:lang="en"><p>Oleg G. Sinyashin</p><p>420088, Kazan</p></bio><email xlink:type="simple">oleg@iopc.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-3906-8841</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Яхваров</surname><given-names>Д. Г.</given-names></name><name name-style="western" xml:lang="en"><surname>Yakhvarov</surname><given-names>D. G.</given-names></name></name-alternatives><bio xml:lang="en"><p>Dmitry G. Yakhvarov</p><p>420088, Kazan</p></bio><email xlink:type="simple">yakhvar@iopc.ru</email><xref ref-type="aff" rid="aff-2"/></contrib></contrib-group><aff xml:lang="en" id="aff-1"><institution>Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences</institution><country>Russian Federation</country></aff><aff xml:lang="en" id="aff-2"><institution>Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences; A.M. Butlerov Institute of Chemistry, Kazan Federal University</institution><country>Russian Federation</country></aff><aff xml:lang="en" id="aff-3"><institution>Laboratory for Structural Studies of Biomacromolecules, FRC Kazan Scientific Center, Russian Academy of Sciences</institution><country>Russian Federation</country></aff><aff xml:lang="en" id="aff-4"><institution>A.M. Butlerov Institute of Chemistry, Kazan Federal University</institution><country>Russian Federation</country></aff><aff xml:lang="en" id="aff-5"><institution>A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences</institution><country>Russian Federation</country></aff><pub-date pub-type="collection"><year>2025</year></pub-date><pub-date pub-type="epub"><day>01</day><month>06</month><year>2025</year></pub-date><volume>16</volume><issue>1</issue><fpage>116</fpage><lpage>122</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Kagilev A.A., Sakhapov I.F., Gafurov Z.N., Kantyukov A.O., Mikhailov I.K., Islamov D.R., Gerasimov A.V., Filippov O.A., Gubaidullin A.T., Soficheva O.S., Sinyashin O.G., Yakhvarov D.G., 2025</copyright-statement><copyright-year>2025</copyright-year><copyright-holder xml:lang="ru">Кагилев А.А., Сахапов И.Ф., Гафуров З.Н., Кантюков А.О., Михайлов И.К., Исламов Д.Р., Герасимов А.В., Филиппов О.А., Губайдуллин А.Т., Софичева О.С., Синяшин О.Г., Яхваров Д.Г.</copyright-holder><copyright-holder xml:lang="en">Kagilev A.A., Sakhapov I.F., Gafurov Z.N., Kantyukov A.O., Mikhailov I.K., Islamov D.R., Gerasimov A.V., Filippov O.A., Gubaidullin A.T., Soficheva O.S., Sinyashin O.G., Yakhvarov D.G.</copyright-holder><license xml:lang="ru" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>Данная работа распространяется под лицензией Creative Commons Attribution 4.0.</license-p></license><license xml:lang="en" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>This work is licensed under a Creative Commons Attribution 4.0 License.</license-p></license></permissions><self-uri xlink:href="https://nanojournal.ifmo.ru/jour/article/view/97">https://nanojournal.ifmo.ru/jour/article/view/97</self-uri><abstract><p>The reaction of glyoxylic acid monohydrate with mesityl(phenyl)phosphine in air led to the formation of mesityl(phenyl)phosphine oxide glycolate. The synthesized mesityl(phenyl)phosphine oxide glycolate has been characterized by various analytical methods including X-ray crystal structure analysis. The analysis of intermolecular interactions in the crystal revealed interesting modes of the noncovalent bonding between pairs of molecules. These intermolecular interactions cause the formation of one-dimensional cylindrical channels with diameter of 1 nm (10 A° ) and provide the crystal with the properties of precise nano-sized crystalline porous material which can be served as the component for precise nanofiltration membranes improving the properties of amorphous polymers which suffer from disordered pore structures and reduced selectivity towards separating molecules.</p></abstract><trans-abstract xml:lang="ru"><p>Реакция моногидрата глиоксиловой кислоты с мезитил(фенил)фосфином на воздухе привела к образованию гликолата оксида мезитил(фенил)фосфина. Синтезированный гликолят оксида мезитил(фенил)фосфина был охарактеризован различными аналитическими методами, кристаллическая структура определена методом рентгеновской дифракции. Анализ межмолекулярных взаимодействий в кристалле выявил интересные типы нековалентных связей между парами молекул. Эти межмолекулярные взаимодействия вызывают образование одномерных цилиндрических каналов диаметром 1 нм (10 Å) и придают кристаллу свойства наноразмерного кристаллического пористого материала с точным размером пор, который может служить компонентом для точных нанофильтрационных мембран, улучшающих свойства аморфных полимеров, имеющих неупорядоченную структуру и пониженную селективность по отношению к разделяемым молекулам</p></trans-abstract><kwd-group xml:lang="ru"><kwd>фосфин</kwd><kwd>фосфиноксид</kwd><kwd>гликолят</kwd><kwd>рентгеновская дифракция</kwd><kwd>нековалентные взаимодействия</kwd></kwd-group><kwd-group xml:lang="en"><kwd>phosphine</kwd><kwd>phosphine oxide</kwd><kwd>glycolate</kwd><kwd>X-ray diffraction</kwd><kwd>noncovalent bonding</kwd></kwd-group><funding-group><funding-statement xml:lang="en">This research was funded by the grant of the Ministry of Science and Higher Education of the Russian Federation for large scientific projects of the priority areas of scientific and technological development (Nr. 075-15-2024-646).</funding-statement></funding-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">de Silva P., Corminboeuf C. Simultaneous Visualization of Covalent and Noncovalent Interactions Using Regions of Density Overlap. J. Chem. Theory Comput., 2014, 10, P. 3745–3756.</mixed-citation><mixed-citation xml:lang="en">de Silva P., Corminboeuf C. Simultaneous Visualization of Covalent and Noncovalent Interactions Using Regions of Density Overlap. J. Chem. Theory Comput., 2014, 10, P. 3745–3756.</mixed-citation></citation-alternatives></ref><ref id="cit2"><label>2</label><citation-alternatives><mixed-citation xml:lang="ru">Johnson E.R., Keinan S., Mori-S´anchez P., Contreras-Garc´ıa J., Cohen A.J., Yang W. Revealing Noncovalent Interactions. J. Am. Chem. Soc., 2010, 132, P. 6498–6506.</mixed-citation><mixed-citation xml:lang="en">Johnson E.R., Keinan S., Mori-S´anchez P., Contreras-Garc´ıa J., Cohen A.J., Yang W. Revealing Noncovalent Interactions. J. Am. Chem. Soc., 2010, 132, P. 6498–6506.</mixed-citation></citation-alternatives></ref><ref id="cit3"><label>3</label><citation-alternatives><mixed-citation xml:lang="ru">Andrez´alov´a L., Orsz´aghov´a Z. Covalent and noncovalent interactions of coordination compounds with DNA: An overview. Journal of Inorganic Biochemistry, 2021, 225, P. 111624.</mixed-citation><mixed-citation xml:lang="en">Andrez´alov´a L., Orsz´aghov´a Z. Covalent and noncovalent interactions of coordination compounds with DNA: An overview. Journal of Inorganic Biochemistry, 2021, 225, P. 111624.</mixed-citation></citation-alternatives></ref><ref id="cit4"><label>4</label><citation-alternatives><mixed-citation xml:lang="ru">Gao X., Zou X., Ma H., Meng S., Zhu G. Highly Selective and Permeable Porous Organic Framework Membrane for CO2 Capture. Advanced Materials, 2014, 26, P. 3644–3648.</mixed-citation><mixed-citation xml:lang="en">Gao X., Zou X., Ma H., Meng S., Zhu G. Highly Selective and Permeable Porous Organic Framework Membrane for CO2 Capture. Advanced Materials, 2014, 26, P. 3644–3648.</mixed-citation></citation-alternatives></ref><ref id="cit5"><label>5</label><citation-alternatives><mixed-citation xml:lang="ru">Hobza P., Rˇ eza´cˇJ. Introduction: Noncovalent Interactions. Chem. Rev., 2016, 116, P. 4911–4912.</mixed-citation><mixed-citation xml:lang="en">Hobza P., Rˇ eza´cˇJ. Introduction: Noncovalent Interactions. Chem. Rev., 2016, 116, P. 4911–4912.</mixed-citation></citation-alternatives></ref><ref id="cit6"><label>6</label><citation-alternatives><mixed-citation xml:lang="ru">Kollman P.A. Noncovalent interactions. Acc. Chem. Res., 1977, 10, P. 365–371.</mixed-citation><mixed-citation xml:lang="en">Kollman P.A. Noncovalent interactions. Acc. Chem. Res., 1977, 10, P. 365–371.</mixed-citation></citation-alternatives></ref><ref id="cit7"><label>7</label><citation-alternatives><mixed-citation xml:lang="ru">Vyas V.S., Vishwakarma M., Moudrakovski I., Haase F., Savasci G., Ochsenfeld C., Spatz J.P., Lotsch B.V. Exploiting Noncovalent Interactions in an Imine-Based Covalent Organic Framework for Quercetin Delivery. Advanced Materials, 2016, 28, P. 8749–8754.</mixed-citation><mixed-citation xml:lang="en">Vyas V.S., Vishwakarma M., Moudrakovski I., Haase F., Savasci G., Ochsenfeld C., Spatz J.P., Lotsch B.V. Exploiting Noncovalent Interactions in an Imine-Based Covalent Organic Framework for Quercetin Delivery. Advanced Materials, 2016, 28, P. 8749–8754.</mixed-citation></citation-alternatives></ref><ref id="cit8"><label>8</label><citation-alternatives><mixed-citation xml:lang="ru">Li P., Ryder M.R., Stoddart J.F. Hydrogen-Bonded Organic Frameworks: A Rising Class of Porous Molecular Materials. Acc. Mater. Res., 2020, 1, P. 77–87.</mixed-citation><mixed-citation xml:lang="en">Li P., Ryder M.R., Stoddart J.F. Hydrogen-Bonded Organic Frameworks: A Rising Class of Porous Molecular Materials. Acc. Mater. Res., 2020, 1, P. 77–87.</mixed-citation></citation-alternatives></ref><ref id="cit9"><label>9</label><citation-alternatives><mixed-citation xml:lang="ru">Shah M., McCarthy M.C., Sachdeva S., Lee A.K., Jeong H.-K. Current Status of Metal–Organic Framework Membranes for Gas Separations: Promises and Challenges. Ind. Eng. Chem. Res., 2012, 51, P. 2179–2199.</mixed-citation><mixed-citation xml:lang="en">Shah M., McCarthy M.C., Sachdeva S., Lee A.K., Jeong H.-K. Current Status of Metal–Organic Framework Membranes for Gas Separations: Promises and Challenges. Ind. Eng. Chem. Res., 2012, 51, P. 2179–2199.</mixed-citation></citation-alternatives></ref><ref id="cit10"><label>10</label><citation-alternatives><mixed-citation xml:lang="ru">Caro J., Noack M. Zeolite membranes – Recent developments and progress. Microporous and Mesoporous Materials, 2008, 115, P. 215–233.</mixed-citation><mixed-citation xml:lang="en">Caro J., Noack M. Zeolite membranes – Recent developments and progress. Microporous and Mesoporous Materials, 2008, 115, P. 215–233.</mixed-citation></citation-alternatives></ref><ref id="cit11"><label>11</label><citation-alternatives><mixed-citation xml:lang="ru">Zhu X., Tian C., Mahurin S.M., Chai S.-H., Wang C., Brown S., Veith G.M., Luo H., Liu H., Dai S. A Superacid-Catalyzed Synthesis of Porous Membranes Based on Triazine Frameworks for CO2 Separation. J. Am. Chem. Soc., 2012, 134, P. 10478–10484.</mixed-citation><mixed-citation xml:lang="en">Zhu X., Tian C., Mahurin S.M., Chai S.-H., Wang C., Brown S., Veith G.M., Luo H., Liu H., Dai S. A Superacid-Catalyzed Synthesis of Porous Membranes Based on Triazine Frameworks for CO2 Separation. J. Am. Chem. Soc., 2012, 134, P. 10478–10484.</mixed-citation></citation-alternatives></ref><ref id="cit12"><label>12</label><citation-alternatives><mixed-citation xml:lang="ru">Carta M., Malpass-Evans R., Croad M., Rogan Y., Jansen J.C., Bernardo P., Bazzarelli F., McKeown N.B. An Efficient Polymer Molecular Sieve for Membrane Gas Separations. Science, 2013, 339, P. 303–307.</mixed-citation><mixed-citation xml:lang="en">Carta M., Malpass-Evans R., Croad M., Rogan Y., Jansen J.C., Bernardo P., Bazzarelli F., McKeown N.B. An Efficient Polymer Molecular Sieve for Membrane Gas Separations. Science, 2013, 339, P. 303–307.</mixed-citation></citation-alternatives></ref><ref id="cit13"><label>13</label><citation-alternatives><mixed-citation xml:lang="ru">Chen L., Zhang B., Chen L., Liu H., Hu Y., Qiao S. Hydrogen-bonded organic frameworks: design, applications, and prospects. Mater. Adv., 2022, 3, P. 3680–3708.</mixed-citation><mixed-citation xml:lang="en">Chen L., Zhang B., Chen L., Liu H., Hu Y., Qiao S. Hydrogen-bonded organic frameworks: design, applications, and prospects. Mater. Adv., 2022, 3, P. 3680–3708.</mixed-citation></citation-alternatives></ref><ref id="cit14"><label>14</label><citation-alternatives><mixed-citation xml:lang="ru">Yang J., Wang J., Hou B., Huang X., Wang T., Bao Y., Hao H. Porous hydrogen-bonded organic frameworks (HOFs): From design to potential applications. Chemical Engineering Journal, 2020, 399, P. 125873.</mixed-citation><mixed-citation xml:lang="en">Yang J., Wang J., Hou B., Huang X., Wang T., Bao Y., Hao H. Porous hydrogen-bonded organic frameworks (HOFs): From design to potential applications. Chemical Engineering Journal, 2020, 399, P. 125873.</mixed-citation></citation-alternatives></ref><ref id="cit15"><label>15</label><citation-alternatives><mixed-citation xml:lang="ru">Arduengo A.J.I., Gamper S.F., Tamm M., Calabrese J.C., Davidson F., Craig H.A. A Bis(carbene)-Proton Complex: Structure of a C-H-C Hydrogen Bond. J. Am. Chem. Soc., 1995, 117, P. 572–573.</mixed-citation><mixed-citation xml:lang="en">Arduengo A.J.I., Gamper S.F., Tamm M., Calabrese J.C., Davidson F., Craig H.A. A Bis(carbene)-Proton Complex: Structure of a C-H-C Hydrogen Bond. J. Am. Chem. Soc., 1995, 117, P. 572–573.</mixed-citation></citation-alternatives></ref><ref id="cit16"><label>16</label><citation-alternatives><mixed-citation xml:lang="ru">Gronert S., Keeffe J.R. Identity Hydride-Ion Transfer from C?H Donors to C Acceptor Sites. Enthalpies of Hydride Addition and Enthalpies of Activation. Comparison with C H C Proton Transfer. An ab Initio Study. J. Am. Chem. Soc., 2005, 127, P. 2324–2333.</mixed-citation><mixed-citation xml:lang="en">Gronert S., Keeffe J.R. Identity Hydride-Ion Transfer from C?H Donors to C Acceptor Sites. Enthalpies of Hydride Addition and Enthalpies of Activation. Comparison with C H C Proton Transfer. An ab Initio Study. J. Am. Chem. Soc., 2005, 127, P. 2324–2333.</mixed-citation></citation-alternatives></ref><ref id="cit17"><label>17</label><citation-alternatives><mixed-citation xml:lang="ru">Krishnamohan Sharma C.V., Broker G.A., Rogers R.D. Polymorphous One-Dimensional Tetrapyridylporphyrin Coordination Polymers Which Structurally Mimic Aryl Stacking Interactions. Journal of Solid State Chemistry, 2000, 152, P. 253–260.</mixed-citation><mixed-citation xml:lang="en">Krishnamohan Sharma C.V., Broker G.A., Rogers R.D. Polymorphous One-Dimensional Tetrapyridylporphyrin Coordination Polymers Which Structurally Mimic Aryl Stacking Interactions. Journal of Solid State Chemistry, 2000, 152, P. 253–260.</mixed-citation></citation-alternatives></ref><ref id="cit18"><label>18</label><citation-alternatives><mixed-citation xml:lang="ru">Duarte M.T., Piedade M.F.M., Robalo M.P., Teixeira A.P.S., Garcia M.H. A supramolecular zigzag chain of organometallic dipoles mediated by PF6-anions. Acta Crystallogr C Cryst Struct Commun, 2005, 61, P. m386–m389.</mixed-citation><mixed-citation xml:lang="en">Duarte M.T., Piedade M.F.M., Robalo M.P., Teixeira A.P.S., Garcia M.H. A supramolecular zigzag chain of organometallic dipoles mediated by PF6-anions. Acta Crystallogr C Cryst Struct Commun, 2005, 61, P. m386–m389.</mixed-citation></citation-alternatives></ref><ref id="cit19"><label>19</label><citation-alternatives><mixed-citation xml:lang="ru">Das S., Bharadwaj P.K. Self-Assembly of a Luminescent Zinc(II) Complex: a Supramolecular Host–Guest Fluorescence Signaling System for Selective Nitrobenzene Inclusion. Inorg. Chem., 2006, 45, P. 5257–5259.</mixed-citation><mixed-citation xml:lang="en">Das S., Bharadwaj P.K. Self-Assembly of a Luminescent Zinc(II) Complex: a Supramolecular Host–Guest Fluorescence Signaling System for Selective Nitrobenzene Inclusion. Inorg. Chem., 2006, 45, P. 5257–5259.</mixed-citation></citation-alternatives></ref><ref id="cit20"><label>20</label><citation-alternatives><mixed-citation xml:lang="ru">Chakravorty S., Platts J.A., Das B.K. Novel C–H C contacts involving 3,5-dimethylpyrazole ligands in a tetracoordinate Co(ii) complex. Dalton Trans., 2011, 40, P. 11605.</mixed-citation><mixed-citation xml:lang="en">Chakravorty S., Platts J.A., Das B.K. Novel C–H C contacts involving 3,5-dimethylpyrazole ligands in a tetracoordinate Co(ii) complex. Dalton Trans., 2011, 40, P. 11605.</mixed-citation></citation-alternatives></ref><ref id="cit21"><label>21</label><citation-alternatives><mixed-citation xml:lang="ru">Kharel S., Bhuvanesh N., Gladysz J.A., Bl¨umel J. New hydrogen bonding motifs of phosphine oxides with a silanediol, a phenol, and chloroform. Inorganica Chimica Acta, 2019, 490, P. 215–219.</mixed-citation><mixed-citation xml:lang="en">Kharel S., Bhuvanesh N., Gladysz J.A., Bl¨umel J. New hydrogen bonding motifs of phosphine oxides with a silanediol, a phenol, and chloroform. Inorganica Chimica Acta, 2019, 490, P. 215–219.</mixed-citation></citation-alternatives></ref><ref id="cit22"><label>22</label><citation-alternatives><mixed-citation xml:lang="ru">Tupikina E.Yu., Bodensteiner M., Tolstoy P.M., Denisov G.S., Shenderovich I.G. P=O Moiety as an Ambidextrous Hydrogen Bond Acceptor. J. Phys. Chem. C, 2018, 122, P. 711–1720.</mixed-citation><mixed-citation xml:lang="en">Tupikina E.Yu., Bodensteiner M., Tolstoy P.M., Denisov G.S., Shenderovich I.G. P=O Moiety as an Ambidextrous Hydrogen Bond Acceptor. J. Phys. Chem. C, 2018, 122, P. 711–1720.</mixed-citation></citation-alternatives></ref><ref id="cit23"><label>23</label><citation-alternatives><mixed-citation xml:lang="ru">Kostin M.A., Pylaeva S.A., Tolstoy P.M. Phosphine oxides as NMR and IR spectroscopic probes for the estimation of the geometry and energy of PO H–A hydrogen bonds. Phys. Chem. Chem. Phys., 2022, 24, P. 7121–7133.</mixed-citation><mixed-citation xml:lang="en">Kostin M.A., Pylaeva S.A., Tolstoy P.M. Phosphine oxides as NMR and IR spectroscopic probes for the estimation of the geometry and energy of PO H–A hydrogen bonds. Phys. Chem. Chem. Phys., 2022, 24, P. 7121–7133.</mixed-citation></citation-alternatives></ref><ref id="cit24"><label>24</label><citation-alternatives><mixed-citation xml:lang="ru">Kostin M.A., Alkhuder O., Xu L., Krutin D.V., Asfin R.E., Tolstoy P.M. Complexes of phosphine oxides with substituted phenols: hydrogen bond characterization based on shifts of P-O stretching bands. Phys. Chem. Chem. Phys., 2024, 26, P. 10234–10242.</mixed-citation><mixed-citation xml:lang="en">Kostin M.A., Alkhuder O., Xu L., Krutin D.V., Asfin R.E., Tolstoy P.M. Complexes of phosphine oxides with substituted phenols: hydrogen bond characterization based on shifts of P-O stretching bands. Phys. Chem. Chem. Phys., 2024, 26, P. 10234–10242.</mixed-citation></citation-alternatives></ref><ref id="cit25"><label>25</label><citation-alternatives><mixed-citation xml:lang="ru">Gafurov Z.N., Zueva E.M., Yakhvarov D.G. Sustainable Synthesis, NMR and Computational Study of Isobutylmesitylphosphine. Chemistry Select, 2021, 6, P. 1833–1837.</mixed-citation><mixed-citation xml:lang="en">Gafurov Z.N., Zueva E.M., Yakhvarov D.G. Sustainable Synthesis, NMR and Computational Study of Isobutylmesitylphosphine. Chemistry Select, 2021, 6, P. 1833–1837.</mixed-citation></citation-alternatives></ref><ref id="cit26"><label>26</label><citation-alternatives><mixed-citation xml:lang="ru">Jerphagnon T., Renaud J.-L., Bruneau C. Chiral monodentate phosphorus ligands for rhodium-catalyzed asymmetric hydrogenation. Tetrahedron: Asymmetry, 2004, 15, P. 2101–2111.</mixed-citation><mixed-citation xml:lang="en">Jerphagnon T., Renaud J.-L., Bruneau C. Chiral monodentate phosphorus ligands for rhodium-catalyzed asymmetric hydrogenation. Tetrahedron: Asymmetry, 2004, 15, P. 2101–2111.</mixed-citation></citation-alternatives></ref><ref id="cit27"><label>27</label><citation-alternatives><mixed-citation xml:lang="ru">Imamoto T., Cr´epy K.V.L., Katagiri K. Optically active 1,1’-di-tert-butyl-2,2’-dibenzophosphetenyl: a highly strained P-stereogenic diphosphine ligand. Tetrahedron: Asymmetry, 2004, 15, P. 2213–2218.</mixed-citation><mixed-citation xml:lang="en">Imamoto T., Cr´epy K.V.L., Katagiri K. Optically active 1,1’-di-tert-butyl-2,2’-dibenzophosphetenyl: a highly strained P-stereogenic diphosphine ligand. Tetrahedron: Asymmetry, 2004, 15, P. 2213–2218.</mixed-citation></citation-alternatives></ref><ref id="cit28"><label>28</label><citation-alternatives><mixed-citation xml:lang="ru">Cheng X., Horton P.N., Hursthouse M.B., Hii K.K. Aminohydroxy phosphine oxide ligands in ruthenium-catalysed asymmetric transfer hydrogenation reactions. Tetrahedron: Asymmetry, 2004, 15, P. 2241–2246.</mixed-citation><mixed-citation xml:lang="en">Cheng X., Horton P.N., Hursthouse M.B., Hii K.K. Aminohydroxy phosphine oxide ligands in ruthenium-catalysed asymmetric transfer hydrogenation reactions. Tetrahedron: Asymmetry, 2004, 15, P. 2241–2246.</mixed-citation></citation-alternatives></ref><ref id="cit29"><label>29</label><citation-alternatives><mixed-citation xml:lang="ru">Methot J.L., Roush W.R. Nucleophilic Phosphine Organocatalysis. Adv Synth Catal, 2004, 346, P. 1035–1050.</mixed-citation><mixed-citation xml:lang="en">Methot J.L., Roush W.R. Nucleophilic Phosphine Organocatalysis. Adv Synth Catal, 2004, 346, P. 1035–1050.</mixed-citation></citation-alternatives></ref><ref id="cit30"><label>30</label><citation-alternatives><mixed-citation xml:lang="ru">Seayad J., List B. Asymmetric organocatalysis. Org. Biomol. Chem., 2005, 3, P. 719.</mixed-citation><mixed-citation xml:lang="en">Seayad J., List B. Asymmetric organocatalysis. Org. Biomol. Chem., 2005, 3, P. 719.</mixed-citation></citation-alternatives></ref><ref id="cit31"><label>31</label><citation-alternatives><mixed-citation xml:lang="ru">Connon S.J. Chiral Phosphoric Acids: Powerful Organocatalysts for Asymmetric Addition Reactions to Imines. Angew Chem Int Ed, 2006, 45, P. 3909–3912.</mixed-citation><mixed-citation xml:lang="en">Connon S.J. Chiral Phosphoric Acids: Powerful Organocatalysts for Asymmetric Addition Reactions to Imines. Angew Chem Int Ed, 2006, 45, P. 3909–3912.</mixed-citation></citation-alternatives></ref><ref id="cit32"><label>32</label><citation-alternatives><mixed-citation xml:lang="ru">Benaglia M., Rossi S. Chiral phosphine oxides in present-day organocatalysis. Org. Biomol. Chem., 2010, 8, P. 3824.</mixed-citation><mixed-citation xml:lang="en">Benaglia M., Rossi S. Chiral phosphine oxides in present-day organocatalysis. Org. Biomol. Chem., 2010, 8, P. 3824.</mixed-citation></citation-alternatives></ref><ref id="cit33"><label>33</label><citation-alternatives><mixed-citation xml:lang="ru">Adams H., Collins R.C., Jones S., Warner C.J.A. Enantioselective Preparation of P-Chiral Phosphine Oxides. Org. Lett., 2011, 13, P. 6576–6579.</mixed-citation><mixed-citation xml:lang="en">Adams H., Collins R.C., Jones S., Warner C.J.A. Enantioselective Preparation of P-Chiral Phosphine Oxides. Org. Lett., 2011, 13, P. 6576–6579.</mixed-citation></citation-alternatives></ref><ref id="cit34"><label>34</label><citation-alternatives><mixed-citation xml:lang="ru">Gafurov Z.N., Musin L.I., Sakhapov I.F., Babaev V.M., Musina E.I., Karasik A.A., Sinyashin O.G., Yakhvarov D.G. The formation of secondary arylphosphines in the reaction of organonickel sigma-complex [NiBr(Mes)(bpy)], where Mes = 2,4,6-trimethylphenyl, bpy = 2,2’-bipyridine, with phenylphosphine. Phosphorus, Sulfur, and Silicon and the Related Elements, 2016, 191, P. 1475–1477.</mixed-citation><mixed-citation xml:lang="en">Gafurov Z.N., Musin L.I., Sakhapov I.F., Babaev V.M., Musina E.I., Karasik A.A., Sinyashin O.G., Yakhvarov D.G. The formation of secondary arylphosphines in the reaction of organonickel sigma-complex [NiBr(Mes)(bpy)], where Mes = 2,4,6-trimethylphenyl, bpy = 2,2’-bipyridine, with phenylphosphine. Phosphorus, Sulfur, and Silicon and the Related Elements, 2016, 191, P. 1475–1477.</mixed-citation></citation-alternatives></ref><ref id="cit35"><label>35</label><citation-alternatives><mixed-citation xml:lang="ru">Sheldrick G.M. SHELXT– Integrated space-group and crystal-structure determination. Acta Crystallogr A Found Adv, 2015, 71, P. 3–8.</mixed-citation><mixed-citation xml:lang="en">Sheldrick G.M. SHELXT– Integrated space-group and crystal-structure determination. Acta Crystallogr A Found Adv, 2015, 71, P. 3–8.</mixed-citation></citation-alternatives></ref><ref id="cit36"><label>36</label><citation-alternatives><mixed-citation xml:lang="ru">Sheldrick G.M. A short history ofSHELX. Acta Crystallogr A Found Crystallogr, 2007, 64, P. 112–122.</mixed-citation><mixed-citation xml:lang="en">Sheldrick G.M. A short history ofSHELX. Acta Crystallogr A Found Crystallogr, 2007, 64, P. 112–122.</mixed-citation></citation-alternatives></ref><ref id="cit37"><label>37</label><citation-alternatives><mixed-citation xml:lang="ru">Macrae C.F. Edgington P.R., McCabe P., Pidcock E., Shields G.P., Taylor R., Towler M., Van De Streek J. Mercury: visualization and analysis of crystal structures. J Appl Crystallogr, 2006, 39, P. 453–457.</mixed-citation><mixed-citation xml:lang="en">Macrae C.F. Edgington P.R., McCabe P., Pidcock E., Shields G.P., Taylor R., Towler M., Van De Streek J. Mercury: visualization and analysis of crystal structures. J Appl Crystallogr, 2006, 39, P. 453–457.</mixed-citation></citation-alternatives></ref><ref id="cit38"><label>38</label><citation-alternatives><mixed-citation xml:lang="ru">www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk)</mixed-citation><mixed-citation xml:lang="en">www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk)</mixed-citation></citation-alternatives></ref><ref id="cit39"><label>39</label><citation-alternatives><mixed-citation xml:lang="ru">EVA v.11.0.0.3. User Manual. SOCABIM, 2005.</mixed-citation><mixed-citation xml:lang="en">EVA v.11.0.0.3. User Manual. SOCABIM, 2005.</mixed-citation></citation-alternatives></ref><ref id="cit40"><label>40</label><citation-alternatives><mixed-citation xml:lang="ru">Spackman P.R., Turner M.J., McKinnon J.J., Wolff S.K., Grimwood D.J., Jayatilaka D., Spackman M.A. CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. J Appl Crystallogr, 2021, 54, P. 1006–1011.</mixed-citation><mixed-citation xml:lang="en">Spackman P.R., Turner M.J., McKinnon J.J., Wolff S.K., Grimwood D.J., Jayatilaka D., Spackman M.A. CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. J Appl Crystallogr, 2021, 54, P. 1006–1011.</mixed-citation></citation-alternatives></ref><ref id="cit41"><label>41</label><citation-alternatives><mixed-citation xml:lang="ru">Mackenzie C.F., Spackman P.R., Jayatilaka D., Spackman M.A. CrystalExplorermodel energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems. IUCrJ, 2017, 4, P. 575–587.</mixed-citation><mixed-citation xml:lang="en">Mackenzie C.F., Spackman P.R., Jayatilaka D., Spackman M.A. CrystalExplorermodel energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems. IUCrJ, 2017, 4, P. 575–587.</mixed-citation></citation-alternatives></ref><ref id="cit42"><label>42</label><citation-alternatives><mixed-citation xml:lang="ru">Grossmann G., Kr¨uger K., Ohms G., Fischer A., Jones P.G., Goerlich J., Schmutzler R. Phosphorus Nuclear Magnetic Shielding Anisotropy and Crystal Structure of (1-Hydroxyalkyl)dimethylphosphine Sulfides. Inorg. Chem., 1997, 36, P. 770–775.</mixed-citation><mixed-citation xml:lang="en">Grossmann G., Kr¨uger K., Ohms G., Fischer A., Jones P.G., Goerlich J., Schmutzler R. Phosphorus Nuclear Magnetic Shielding Anisotropy and Crystal Structure of (1-Hydroxyalkyl)dimethylphosphine Sulfides. Inorg. Chem., 1997, 36, P. 770–775.</mixed-citation></citation-alternatives></ref></ref-list><fn-group><fn fn-type="conflict"><p>The authors declare that there are no conflicts of interest present.</p></fn></fn-group></back></article>
