Halogenation and mu H Tautomerism of 7-Benzyl-7,8-dicarba-nido-undecaborate(-1) Anion Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2019, Volume: 55, Number: 10, Pages: 1495-1503 Pages count : 9 DOI: 10.1134/S1070428019100075 | ||||
| Tags | carborane; tautomerism; nuclear magnetic resonance; halogenation | ||||
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Abstract:
y Deboration of 1-PhCH2-1,2-C2B10H11 by heating in ethanolic potassium hydroxide afforded Me4N+ [7-PhCH2-7,8-C2B9H11](-) which was treated with excess halosuccinimide (NCS, NBS) in acetonitrile or with elemental iodine or bromine in methanol to obtain Me4N+ [7-PhCH2-9,11-X-2-7,8-C2B9H9](-) (X = Cl, Br, I). The reaction of 1-PhCH2-1,2-C2B10H11 with an equimolar amount of iodine gave a mixture of Me4N+center dot[7-PhCH2-11-I-7,8-C2B9H10](-) and Me4N+[7-C6H5CH2-9-I-7,8-C2B9H10](-) at a ratio 1 : 1.8 due to steric effect of the benzyl substituent. The B-11 chemical shifts of each mu-H tautomer of Me4N+ [7-PhCH2-9,11-X-2-7,8-C2B9H9](-)(X = H, F, Cl, Br, I) were calculated at the DFT level of theory, and their contributions to the average B-11 NMR spectrum and the corresponding tautomeric equilibrium constants were determined.
Cite:
Rudakov D.A.
, Genaev A.M.
, Dikusar E.A.
, Zvereva T.D.
, Zubreichuk Z.P.
, Potkin V.I.
Halogenation and mu H Tautomerism of 7-Benzyl-7,8-dicarba-nido-undecaborate(-1) Anion
Russian Journal of Organic Chemistry. 2019. V.55. N10. P.1495-1503. DOI: 10.1134/S1070428019100075 WOS Scopus РИНЦ OpenAlex
Halogenation and mu H Tautomerism of 7-Benzyl-7,8-dicarba-nido-undecaborate(-1) Anion
Russian Journal of Organic Chemistry. 2019. V.55. N10. P.1495-1503. DOI: 10.1134/S1070428019100075 WOS Scopus РИНЦ OpenAlex
Original:
Рудаков Д.А.
, Генаев А.М.
, Дикусар Е.А.
, Зверева Т.Д.
, Зубрейчук З.П.
, Поткин В.И.
Галогенирование и μh-таутомерия 7-бензил-7,8-дикарба-нидо-ундекаборат(-1) аниона
Журнал органической химии (RUSS J ORG CHEM+). 2019. Т.55. №10. С.1540-1550. DOI: 10.1134/S0514749219100070 РИНЦ OpenAlex
Галогенирование и μh-таутомерия 7-бензил-7,8-дикарба-нидо-ундекаборат(-1) аниона
Журнал органической химии (RUSS J ORG CHEM+). 2019. Т.55. №10. С.1540-1550. DOI: 10.1134/S0514749219100070 РИНЦ OpenAlex
Dates:
| Published print: | Oct 1, 2019 |
| Published online: | Dec 9, 2019 |
Identifiers:
| Web of science: | WOS:000511211100007 |
| Scopus: | 2-s2.0-85076862066 |
| Elibrary: | 43220776 |
| OpenAlex: | W2995540781 |