Hydrogen-bonding between benzoic acid and an N,N′-diethyl-substituted benzamidine

Arno Kraft; Lars Peters; Harold R. Powell

doi:10.1016/S0040-4020(02)00301-0

Hydrogen-bonding between benzoic acid and an N,N′-diethyl-substituted benzamidine

Arno Kraft, Lars Peters, Harold R. Powell

School of Engineering & Physical Sciences

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

42 Citations (Scopus)

Abstract

The synthesis and crystal structure of 4,N,N'-triethylbenzamidinium benzoate is reported in which the benzoate anion and the (E,E)-configured amidinium group are linked through two hydrogen bonds (with an N·middot;middot;O distance of 2.723Å). Since an amidine (E,E) isomer was also observed for chloroform solutions of the complex, the binding mode in the crystal and in solution was analogous to that reported for unsubstituted amidines. The strong basicity of the N,N'-diethyl-substituted benzamidine (pK_a 11.99±0.02 in water-dioxane, 1:1) was evident from potentiometric titrations. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	3499-3505
Number of pages	7
Journal	Tetrahedron
Volume	58
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4020(02)00301-0
Publication status	Published - 29 Apr 2002

Keywords

Amidine
Binding
Complexation
Crystal structure
Supramolecular

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10.1016/S0040-4020(02)00301-0

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title = "Hydrogen-bonding between benzoic acid and an N,N′-diethyl-substituted benzamidine",

abstract = "The synthesis and crystal structure of 4,N,N'-triethylbenzamidinium benzoate is reported in which the benzoate anion and the (E,E)-configured amidinium group are linked through two hydrogen bonds (with an N·middot;middot;O distance of 2.723{\AA}). Since an amidine (E,E) isomer was also observed for chloroform solutions of the complex, the binding mode in the crystal and in solution was analogous to that reported for unsubstituted amidines. The strong basicity of the N,N'-diethyl-substituted benzamidine (pKa 11.99±0.02 in water-dioxane, 1:1) was evident from potentiometric titrations. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

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TY - JOUR

T1 - Hydrogen-bonding between benzoic acid and an N,N′-diethyl-substituted benzamidine

AU - Kraft, Arno

AU - Peters, Lars

AU - Powell, Harold R.

PY - 2002/4/29

Y1 - 2002/4/29

N2 - The synthesis and crystal structure of 4,N,N'-triethylbenzamidinium benzoate is reported in which the benzoate anion and the (E,E)-configured amidinium group are linked through two hydrogen bonds (with an N·middot;middot;O distance of 2.723Å). Since an amidine (E,E) isomer was also observed for chloroform solutions of the complex, the binding mode in the crystal and in solution was analogous to that reported for unsubstituted amidines. The strong basicity of the N,N'-diethyl-substituted benzamidine (pKa 11.99±0.02 in water-dioxane, 1:1) was evident from potentiometric titrations. © 2002 Elsevier Science Ltd. All rights reserved.

AB - The synthesis and crystal structure of 4,N,N'-triethylbenzamidinium benzoate is reported in which the benzoate anion and the (E,E)-configured amidinium group are linked through two hydrogen bonds (with an N·middot;middot;O distance of 2.723Å). Since an amidine (E,E) isomer was also observed for chloroform solutions of the complex, the binding mode in the crystal and in solution was analogous to that reported for unsubstituted amidines. The strong basicity of the N,N'-diethyl-substituted benzamidine (pKa 11.99±0.02 in water-dioxane, 1:1) was evident from potentiometric titrations. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Amidine

KW - Binding

KW - Complexation

KW - Crystal structure

KW - Supramolecular

UR - http://www.scopus.com/inward/record.url?scp=0037193095&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(02)00301-0

DO - 10.1016/S0040-4020(02)00301-0

M3 - Article

SN - 0040-4020

VL - 58

SP - 3499

EP - 3505

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -

Hydrogen-bonding between benzoic acid and an N,N′-diethyl-substituted benzamidine

Abstract

Keywords

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