Hydrogen-bonded dimers in dipyrrinones and acyldipyrrinones

M. T. Huggins; D. A. Lightner

doi:10.1007/s007060170131

Hydrogen-bonded dimers in dipyrrinones and acyldipyrrinones

M. T. Huggins, D. A. Lightner

University of Nevada, Reno

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

38 Scopus citations

Abstract

A crystal structure determination of the 9-acyl-dipyrrinone 9-butanoyl-2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one indicates the presence of intermolecularly hydrogen-bonded dimers; however, in CHCl₃ solution the pigment is monomeric as determined by vapor pressure osmometry measurements. Lacking an alkyl group at C(8), the 9-acyl-dipyrrinone exhibits only a weak tendency to form dimers in CHCl₃ (K_A ∼ 60 M^-1) as determined by analysis of variable temperature ¹H NMR data. In contrast, when the 9-acyl group is replaced by formyl or when the acyl group is fixed in a syn orientation to the pyrrole NH, the dipyrrinone is strongly prone to dimerization in CHCl₃.

Original language	English
Pages (from-to)	203-221
Number of pages	19
Journal	Monatshefte fur Chemie
Volume	132
Issue number	2
DOIs	https://doi.org/10.1007/s007060170131
State	Published - 2001
Externally published	Yes

Scopus Subject Areas

General Chemistry

Keywords

Hydrogen bonding
Pyrrole
Vapor pressure osmometry
X-Ray structure

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10.1007/s007060170131

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title = "Hydrogen-bonded dimers in dipyrrinones and acyldipyrrinones",

abstract = "A crystal structure determination of the 9-acyl-dipyrrinone 9-butanoyl-2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one indicates the presence of intermolecularly hydrogen-bonded dimers; however, in CHCl3 solution the pigment is monomeric as determined by vapor pressure osmometry measurements. Lacking an alkyl group at C(8), the 9-acyl-dipyrrinone exhibits only a weak tendency to form dimers in CHCl3 (KA ∼ 60 M-1) as determined by analysis of variable temperature 1H NMR data. In contrast, when the 9-acyl group is replaced by formyl or when the acyl group is fixed in a syn orientation to the pyrrole NH, the dipyrrinone is strongly prone to dimerization in CHCl3.",

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T1 - Hydrogen-bonded dimers in dipyrrinones and acyldipyrrinones

AU - Huggins, M. T.

AU - Lightner, D. A.

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N2 - A crystal structure determination of the 9-acyl-dipyrrinone 9-butanoyl-2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one indicates the presence of intermolecularly hydrogen-bonded dimers; however, in CHCl3 solution the pigment is monomeric as determined by vapor pressure osmometry measurements. Lacking an alkyl group at C(8), the 9-acyl-dipyrrinone exhibits only a weak tendency to form dimers in CHCl3 (KA ∼ 60 M-1) as determined by analysis of variable temperature 1H NMR data. In contrast, when the 9-acyl group is replaced by formyl or when the acyl group is fixed in a syn orientation to the pyrrole NH, the dipyrrinone is strongly prone to dimerization in CHCl3.

AB - A crystal structure determination of the 9-acyl-dipyrrinone 9-butanoyl-2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one indicates the presence of intermolecularly hydrogen-bonded dimers; however, in CHCl3 solution the pigment is monomeric as determined by vapor pressure osmometry measurements. Lacking an alkyl group at C(8), the 9-acyl-dipyrrinone exhibits only a weak tendency to form dimers in CHCl3 (KA ∼ 60 M-1) as determined by analysis of variable temperature 1H NMR data. In contrast, when the 9-acyl group is replaced by formyl or when the acyl group is fixed in a syn orientation to the pyrrole NH, the dipyrrinone is strongly prone to dimerization in CHCl3.

KW - Hydrogen bonding

KW - Pyrrole

KW - Vapor pressure osmometry

KW - X-Ray structure

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DO - 10.1007/s007060170131

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Hydrogen-bonded dimers in dipyrrinones and acyldipyrrinones

Abstract

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Keywords

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