Intra- and inter-molecular carboranyl C-H•••N hydrogen bonds in pyridyl-containing ortho-carboranes

被引：101

作者：

Alekseyeva, ES ^{[1
]}

Batsanov, AS ^{[1
]}

Boyd, LA ^{[1
]}

Fox, MA ^{[1
]}

Hibbert, TG ^{[1
]}

Howard, JAK ^{[1
]}

MacBride, JAH ^{[1
]}

Mackinnon, A ^{[1
]}

Wade, K ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

来源：

DALTON TRANSACTIONS | 2003年 / 03期

关键词：

D O I：

10.1039/b209931d

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Four C-substituted derivatives of ortho-carborane, 1-R-1,2-C2B10H11, where R = 2'-pyridyl (1), 2'-picolyl (2), 5'-bromo-2'-pyridyl (3) or 3'-pyridyl (4) have been prepared using adaptations of standard procedures, and structurally characterised by single crystal X-ray diffraction studies in an exploration of C-H...N hydrogen bonding effects involving their carborane CH units. Calculations at the MP2/6-31G* level of theory were used to assess the strength of the hydrogen bonding detected, and calculated NMR shifts at the GIAO-B3LYP/6-311G* level were compared with measured C-H shifts to show that intramolecular C-H...N hydrogen bonding persisted in solution in the case of compound 1. The value of IR C-H stretching frequencies for probing hydrogen bonding in these systems was also studied. An unsuccessful attempt to convert compound 3 into a macrocyclic species (C2B10H10C5H3N)(3) in which three ortho-carborane units are linked through 2,5-disubstituted pyridine rings is also described.

引用

页码：475 / 482

页数：8

共 36 条

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