Features of the Pnictogen Bonds Formed by Neighboring Nitro Groups in Crystals

Сергей Александрович Собалев, Юрий Васильевич Матвейчук, Екатерина Владимировна Барташевич

Аннотация


Особенности пниктогенных связей O…N рассмотрены с позиций анализа различных геометрических ориентаций соседних нитрогрупп NO2…NO2, наблюдаемых в молекулярных кристаллах. «Идеализированная» для пниктогенной связи ориентация, когда неподеленная пара электронов атома О одной нитрогруппы направлена на электрофильный сайт атома N другой, и «стэкинг»-взаимодействие, для которого характерна параллельная укладка нитрогрупп, отличаются особенностями распределения электронной плотности и электростатического потенциала. Примененный электронный критерий, полученный с помощью квантово-химических расчетов с периодическими граничными условиями, подтвердил, что для рассмотренных О…N взаимодействий выполняется необходимое условие их отнесения к пниктогенным связям.

Ключевые слова


пниктогенная связь; нитрогруппа; электростатический потенциал; электронная плотность; лапласиан электронной плотности

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Литература


Legon A.C. Tetrel, Pnictogen and Chalcogen Bonds Identified in the Gas Phase before they had Names: A Systematic Look at Non-Covalent Interactions. Phys. Chem. Chem. Phys., 2017, vol. 19, no. 23, pp. 14884–14896. DOI: 10.1039/c7cp02518a.

Cavallo G, Metrangolo P., Pilati T., Resnati, G., Terraneo, G. Naming Interactions from the Electrophilic Site. Cryst. Growth Des., 2014, vol. 14, no. 6, pp. 2697–2702. DOI: 10.1021/cg5001717.

Desiraju G.R., Ho P.S., Kloo L., Legon A.C., Marquardt R., Metrangolo P., Politzer P.A., Resnati G., Rissanen K. Definition of the halogen bond. Pure Appl. Chem., 2013, vol. 85, no. 8, pp. 1711–1713.

Reed A.E., Curtiss L.A., Weinhold F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint. Chem. Rev., 1988, vol. 88, no. 6, pp. 899–926. DOI: 10.1021/cr00088a005.

Bader R.F.W. Atoms in Molecules: A Quantum Theory, Clarendon Press, 1990. vol. 22, 438 p.

Grice M.E., Murray J.S., Politzer P. Calculated Surface Electrostatic Potentials of Molecular Sieve Models Containing SiO4, A1O4 and PO4 Units. J. Mol. Graphics., 1994, vol. 12, no. 3, pp. 169–171.

Becke A.D., Edgecombe K.E. A Simple Measure of Electron Localization in Atomic and Mo-lecular Systems. J. Chem. Phys., 1990. vol. 92, no. 9, pp. 5397–5403. DOI: 10.1063/1.458517.

Silvi B., Savin A. Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions, Nature, 1994, vol. 371, no. 6499, pp. 683–686. DOI: 10.1038/371683a0

Sanchez-Sanz G., Trujillo C., Alkorta I., Elguero J. Electron Density Shift Description of Non-Bonding Intramolecular Interactions. Comput. Theor. Chem., 2012, vol. 991, no. 3, pp. 124–133. DOI: 10.1016/j.comptc.2012.04.007.

Johnson E.R., Keinan S., Mori-Sanchez P., Contreras-Garcia J., Cohen A.J., Yang W. Revealing Non-Covalent Interaction. J. Am. Chem. Soc., 2010. vol. 132, no. 18, pp. 6498–6506. DOI: 10.1021/ja100936w.

Politzer P., Murray J.S. An Overview of Strengths and Directionalities of Noncovalent Interactions: σ-Holes and ρ-Holes. Crystals, 2019, vol. 9, no. 3, p. 165. DOI: 10.3390/cryst9030165.

Sanchez-Sanz G., Trujillo C., Alkorta I., Elguero J. Intramolecular Pnicogen Interactions in Phosphorus and Arsenic Analogues of Proton Sponges. Phys. Chem. Chem. Phys., 2014, vol. 16, no. 30. pp. 15900–15909. DOI: 10.1039/c4cp01072h.

Sanchez-Sanz G., Trujillo C., Alkorta I., Elguero J. Competition between Intramolecular Hy-drogen and Pnictogen Bonds in Protonated Systems. Theor. Chem. Acc., 2016, vol. 135, no. 5, p. 140. DOI: 10.1007/s00214-016-1895-8.

Sanchez-Sanz G., Trujillo C., Alkorta I., Elguero J. Modulating Intramolecular P•••N Pnictogen Interactions. Phys. Chem. Chem. Phys., 2016, vol. 18, no. 13, pp. 9148–9160. DOI: 10.1039/c6cp00227g.

Bader R.F.W. Atoms in Molecules: A Quantum Theory. Oxford University Press, New York, 1990, 458 p.

Bader R.F.W. A quantum theory of molecular structure and its applications. Chem. Rev., 1991, vol. 91, no. 5, pp. 893–928. DOI: 10.1021/cr00005a013.

Bader R.F.W. A Bond Path: A Universal Indicator of Bonded Interactions. J. Phys. Chem. A, 1998, vol. 102, no. 37, pp. 7314–7323. DOI: 10.1021/jp981794v.

Popelier P.L.A. Atoms in Molecules. An Introduction. Harlow, Addison Wesley Longman, 2000, 188 p.

Matta C.F., Boyd R.J. The Quantum Theory of Atoms in Molecules. Wiley-VCH, Weinheim, 2007, vol. 46, no. 36, 567 p.

Bader R.F.W. Bond Paths Are Not Chemical Bonds. J. Phys. Chem. A, 2009, vol. 113, no. 38, pp. 10391–10396.

Bader R.F.W. Definition of Molecular Structure: By Choice or by Appeal to Observation? J. Phys. Chem. A, 2010, vol. 114, no. 28, pp. 7431–7444.

Fanfrik J., Zierkiewicz W., Svec P., Ruzickova Z., Rezac J., Michalczyk M., Ruzicka A., Michalska D., Hobza P. Pnictogen Bonding in Pyrazine•PnX5 (Pn = P, As, Sb and X = F, Cl, Br) com-plexes. J. Mol. Model., 2017, vol. 23, no. 11, p. 328. DOI: 10.1007/s00894-017-3502-x.

Fanfrik J., Hnyk D. Dihalogen and Pnictogen Bonding in Crystalline Icosahedral Phosphaboranes. Crystals, 2018, vol. 8, no. 10. p. 390. DOI: 10.3390/cryst8100390.

Joshi P.R., Ramanathan N., Sundararajan K., Sankaran K. Evidence for Phosphorus Bonding in Phosphorus Trichloride–Methanol Adduct: A Matrix Isolation Infrared and ab Initio Computational Study.J. Phys. Chem., 2015, vol. 119, no. 14, pp. 3440–3451. DOI: 10.1021/jp511156d.

Scilabra P., Terraneo G., Resnati G. Fluorinated Elements of Group 15 as Pnictogen Bond Donor Sites. J. Fluor. Chem., 2017, vol. 203, no. 11, pp. 62–74. DOI: 10.1016/j.jfluchem.2017.10.002.

Bauza A., Sharko A.V., Senchyk G.A., Rusanov E.B., Frontera A., Domasevitch K.V. π-Hole Interactions at Work: Crystal Engineering with Nitro-Derivatives. CrystEngComm., 2017, vol. 19, no. 14, pp. 1933–1937. DOI: 10.1039/C7CE00267J.

Bauza A., Mooibroek T.J., Frontera A. Directionality of π-Holes in Nitro Compounds. Chem. Comm., 2015, vol. 51, no. 8, pp. 1491–1493. DOI: 10.1039/C4CC09132A.

Bauza A., Mooibroek T.J., Frontera A. NO3– Anions Can Act as Lewis Acid in the Solid State. Nat. Commun., 2017, vol. 8, no. 2, p. 14522. DOI: 10.1038/ncomms14522.

Bauza A., Frontera A., Mooibroek T.J. π-Hole Interactions Involving Nitro Compounds: Directionality of Nitrate Esters. Crys. Growth Des., 2016, vol. 16, no. 9, pp. 5520–5524. DOI: 10.1021/acs.cgd.6b00989.

Wang Y., Li X., Zeng Y. Theoretical Insights into the p-Hole Interactions in the Complexes Containing Triphosphorus Hydride (P3H3) and Its Derivatives. Acta Cryst., 2017, vol. B73, no. 2, pp. 195–202. DOI: 10.1107/S2052520616019223.

Trujillo C., Sanchez-Sanz G., Alkorta I., Elguero J. Halogen, Chalcogen and Pnictogen Interactions in (XNO2)2 Homodimers (X = F, Cl, Br, I). New J. Chem., 2015, vol. 39, no. 9, pp. 6791–6802. DOI: 10.1039/C5NJ00600G.

Montisci F., Lanza A., Casati N., Macchi P. Testing Soft Donor-Acceptor Intermolecular Interactions with High Pressure. Acta Cryst. A., 2016, vol. 72, no. 8, p. 400. DOI: 10.1107/S205327331609416X.

Montisci F., Lanza A., Casati N., Macchi P. NO2•••NO2 Contacts under Compression: Testing the Forces in Soft Donor–Acceptor Interactions. Cryst. Growth Des., 2018, vol. 18, no. 12, pp. 7579–7589. DOI: 10.1021/acs.cgd.8b01392.

Dovesi R., Saunders V.R., Roetti C. CRYSTAL14 User’s Manual. Torino: University of Torino, 2014, 382 p.

Kostenetskiy P., Semenikhina P. SUSU Supercomputer Resources for Industry and Fundamental Science. Chelyabinsk: Global Smart Industry Conference (GloSIC), 2018, pp. 1–7.

Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery Jr J.A. General Atomic and Molecular Electronic Structure System. J. Comp. Chem., 1993, vol. 14, no. 11, pp. 1347–1363. DOI: 10.1002/jcc.540141112.

Gatti C., Casassa S. Topond14 User’s Manual, Torino: University of Torino, 2014, 53 p.

Groom C.R., Bruno I.J., Lightfoot M.P. The Cambridge Structural Database. Acta Cryst. B., 2016, vol. 72, no. 4, pp. 171–179. DOI: 10.1107/S2052520616003954.

Bartashevich E.V., Mukhitdinova S.E., Yushina I.D., Tsirelson V.G. Electronic Criterion for Categorizing the Chalcogen and Halogen Bonds: Sulfur–Iodine Interactions in Crystals. Acta Cryst. B., 2019, vol. 75, pp. 117–126. DOI: 10.1107/S2052520618018280.

Bartashevich E.V., Yushina I.D., Kropotina K.K., Muhitdinova S.E., Tsirelson V.G. Testing the Tools for Revealing and Characterizing the Iodine-Iodine Halogen Bond in Crystals. Acta Cryst. B., 2017, vol. 73, pp. 217–226. DOI: 10.1107/S2052520617002931.


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