Unusually weak binding interactions in tetrazole-amidine complexes

被引：24
|
作者：
Tominey, AF [1 ]
Docherty, PH [1 ]
Rosair, GM [1 ]
Quenardelle, R [1 ]
Kraft, A [1 ]
机构：
[1] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 07期
关键词：
D O I：
10.1021/ol053072+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tetrazoles frequently replace carboxylic acids in pharmaceutical drugs. However, while the binding modes of tetrazolate and carboxylate anions in amidinium complexes turns out to be similar, the association constant of the former is 2-3 orders of magnitude smaller in DMSO. Crystal structures revealed that the (NH)-H-...-N hydrogen bonds in amidinium tetrazolates are bent (162 degrees and 169 degrees) and noticeably longer ((NN)-N-... 2.96 angstrom) than corresponding hydrogen bonds in both amidinium carboxylates and ammonium tetrazolates.
引用
收藏
页码：1279 / 1282
页数：4
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