Unusually weak binding interactions in tetrazole-amidine complexes

Alan F. Tominey; Paul H. Docherty; Georgina M. Rosair; Romain Quenardelle; Arno Kraft

doi:10.1021/ol053072+

Unusually weak binding interactions in tetrazole-amidine complexes

Alan F. Tominey, Paul H. Docherty, Georgina M. Rosair, Romain Quenardelle, Arno Kraft

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

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 N?H-N hydrogen bonds in amidinium tetrazolates are bent (162° and 169°) and noticeably longer (N?N 2.96 Å) than corresponding hydrogen bonds in both amidinium carboxylates and ammonium tetrazolates. © 2006 American Chemical Society.

Original language	English
Pages (from-to)	1279-1282
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	7
DOIs	https://doi.org/10.1021/ol053072+
Publication status	Published - 30 Mar 2006

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title = "Unusually weak binding interactions in tetrazole-amidine complexes",

abstract = "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 N?H-N hydrogen bonds in amidinium tetrazolates are bent (162° and 169°) and noticeably longer (N?N 2.96 {\AA}) than corresponding hydrogen bonds in both amidinium carboxylates and ammonium tetrazolates. {\textcopyright} 2006 American Chemical Society.",

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AU - Tominey, Alan F.

AU - Docherty, Paul H.

AU - Rosair, Georgina M.

AU - Quenardelle, Romain

AU - Kraft, Arno

PY - 2006/3/30

Y1 - 2006/3/30

N2 - 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 N?H-N hydrogen bonds in amidinium tetrazolates are bent (162° and 169°) and noticeably longer (N?N 2.96 Å) than corresponding hydrogen bonds in both amidinium carboxylates and ammonium tetrazolates. © 2006 American Chemical Society.

AB - 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 N?H-N hydrogen bonds in amidinium tetrazolates are bent (162° and 169°) and noticeably longer (N?N 2.96 Å) than corresponding hydrogen bonds in both amidinium carboxylates and ammonium tetrazolates. © 2006 American Chemical Society.

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U2 - 10.1021/ol053072+

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SP - 1279

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JO - Organic Letters

JF - Organic Letters

IS - 7

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Unusually weak binding interactions in tetrazole-amidine complexes

Abstract

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