vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2021-11-2-178-186vuzbiochemi-591Research ArticleХИМИЧЕСКИЕ НАУКИCHEMICAL SCIENCESНеподелённая электронная пара сурьмы как стереоэлектронный барьер на пути к стибатрануAntimony lone electronic pair as a stereoelectronic barrier to stibatraneБарышокВ. П.BaryshokV. P.

Барышок Виктор Петрович - доктор химических наук, профессор, профессор кафедры химической технологии.

664074, Иркутск, ул. Лермонтова, 83.

Viktor P. Baryshok, - Dr. Sci. (Chemistry), Professor, Chemical Technology Department, Irkutsk National Research Technical University.

83, Lermontov St., Irkutsk, 664074.

baryvik@yandex.ruЗельбстЭ. А.Zel'bstE. A.

Зельбст Элеонора Абрамовна - кандидат химических наук, доцент кафедры физики.

664003, Иркутск, ул. К. Маркса, 1.

Eleonora A. Zel'bst - Cand. Sci. (Chemistry), Associate Professor, Physics Department, Pedagogical Institute, Irkutsk State University.

1, K. Marks St., Irkutsk, 664003.

zelbst@rambler.ruИркутский национальный исследовательский технический университетРоссияIrkutsk National Research Technical UniversityRussian FederationПедагогический институт Иркутского государственного университетаРоссияPedagogical Institute of Irkutsk State UniversityRussian Federation202101072021112178186Copyright © Барышок В.П., Зельбст Э.А., 20212021Барышок В.П., Зельбст Э.А.Baryshok V.P., Zel'bst E.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/591

С целью исследования влияния неподелённой электронной пары 5s2 атома сурьмы на результат реакции трифторида сурьмы с триэтаноламином в присутствии метилата натрия уточнена кристаллическая структура продукта реакции - 2-фтор-6-(2’-гидрооксиэтил)-1,3-Диокса-6-аза-2-стибациклооктана (1-фтор-2-гидростибатрана) FSb(OCH2CH2)2NCH2CH2OH. В структуре данного соединения атом водорода 2-гидроксиэтильной группы каждой молекулы образует межмолекулярную водородную связь с кислородным атомом одного из пятичленных полуциклов SbOCH2CH2N соседней молекулы. Геометрия обоих пятичленных гетероциклов N-C-C-O-Sb, замкнутых трансаннулярной связью N→Sb в молекуле 1 -фтор-2-гидростибатрана, практически одинакова. Межатомные расстояния С-O, C-C, N-C и валентные углы в двух эндоциклических фрагментах (NCCOSb) соизмеримы с наблюдаемыми в силатранах RSi(OCH2CH2)3N. Координационный полиэдр атома Sb может быть представлен как переходный от бисфеноида до тригональной пирамиды Sb(O3)N с атомом азота в вершине и тремя атомами кислорода в основании. Длина трансаннулярной координационной связи N→Sb равна 2,402(4) Å, что на 0,40 Å больше стандартной длины ковалентной связи Sb-N. Связь Sb-F (1,997(4) А) на 0,12 Å длиннее, чем в молекуле SbF3, и незначительно короче значения Sb-Fax (2,028(3) Å) в кристаллическом комплексе SbF3-Gly. Атом фтора существенно отклонен от оси N→Sb в сторону атомов О(1) и О(2). Атом кислорода 2-гидроксиэтильной группы отстоит от атома Sb на расстоянии 2,899(3) Å, промежуточном между длиной валентной связи и суммой ван-дер-ваальсовых радиусов этих атомов. Вкупе с положением атома F это позволяет предположить кристаллическую структуру 1-фтор-2-гидростибатрана как «замороженное» состояние нуклеофильной атаки атома кислорода типа SNi (Sb), незавершенной вследствие его отталкивания неподелённой электронной парой 5s2 атома сурьмы.

To examine the effect of 5s2 lone electron pair of antimony atom on the reaction of antimony trifluoride and triethanolamine in the presence of sodium methylate, the crystal structure of the reaction product -2-fluoro-6-(2-hydroxyethyl)-1,3-dioxa-6-aza-2-stibacy-cylooctane (1-fluoro-2-hydrostibatrane) FSb (OCH2CH2)2NCH2CH2OH) was confirmed. In the compound structure, the hydrogen atom of the 2-hydtoxyethyl group of each molecule forms an intermolecular hydrogen bond with the oxygen atom of one of the five-membered SbOCH2CH2N half-cycles in a neighbouring molecule. A geometry of both five-member N-C-C-O-Sb heterocycles, end-capped by transannular N→Sb bond in the 1-fluoro-2-hydrostibatrane molecule, is almost identical. C-O, C-C, N-C interatomic distances and valence angles in two endocyclic units (NCCOSb) are comparable to those observed in RSi(OCH2CH2)3N silatranes. A coordination polyhedron of the Sb atom can be represented as a transition from a bisphenoid to Sb(O3)N trigonal pyramid, with a nitrogen atom at the apex and three oxygen atoms in the base. The N→Sb transannular coordinate bond length is 2.402(4) Å, which is 0.40 Å greater than the Sb-N covalent bond standard length. The Sb-F bond (1.997(4) Å) is 0.12 Å longer than that in the SbF3 molecule, and insignificantly shorter than that of the Sb-Fax (2.028(3) Å) in the SbF3Gly crystalline complex. The fluorine atom substantially strays from the N→Sb axis to the direction of O(1) and O(2) atoms. The oxygen atom of the 2-hydroxyethyl group lies at a distance of 2.899(3) A from that of Sb, intermediate between the valence bond length and the sum of the Van der Waals radii of these atoms. Combined with the F atom position, one can assume the 1-fluoro-2-hydrostibatrane crystal structure as a “frozen” state of the SNi(Sb) type nucleophilic attack of the oxygen atom, uncompleted because of its repulsion by the 5s2 lone electronic pair of antimony atom.

2-фтор-6-(2’-гидроксиэтил)-13-диокса-6-аза-2-стибациклооктан1-фтор-2-гидростибатранкристаллическая структурамежмолекулярная водородная связьнуклеофильная атака типа SNi (Sb)2-fluoro-6-(2-hydroxyethyl)-13-dioxa-6-aza-2-stibacy-cylooctane1-fluoro-2-hydrostibatranecrystal structureintermolecular hydrogen bondSNi(Sb) type nucleophilic attackАвторы благодарят И.В. Стерхову, к.х.н., старшего научного сотрудника лаборатории структурных исследований Иркутского института химии им. А.Е. Фаворского СО РАН, за уточнение экспериментальных данных кристаллической структуры.The authors are grateful to I.V. Sterkhov, Cand. Sci., Senior Researcher, Structural Research Laboratory, A.E. Favorsky Irkutsk Institute of Chemistry SB RAS, for the refinement of the experimental data on the crystal structure.ReferencesVoit E.I., Udovenko A.A., Kovaleva E.V., Makarenko N.V., Zemnukhova L.A., Beleneva I.A. 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The authors declare that there are no conflicts of interest present.