With regard to the hydrogen bonding in complexes of pyridylureas, less is more. A role for shape complementarity and CH⋯O interactions?

Jordan R. Quinn; Steven C. Zimmerman

doi:10.1021/ol0495016

With regard to the hydrogen bonding in complexes of pyridylureas, less is more. A role for shape complementarity and CH⋯O interactions?

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Abstract

A pyridylurea·tetraazaanthracenedione complex with three hydrogen bonds is more stable than an analogous complex with four hydrogen bonds. An X-ray analysis and modeling suggests a steric mismatch destabilizing the latter and a CH⋯O contact enhancing the stability of the former.

Original language	English (US)
Pages (from-to)	1649-1652
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/ol0495016
State	Published - May 13 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0495016

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Cite this

@article{e290059d789a434a85fcfd6a6bc7d076,

title = "With regard to the hydrogen bonding in complexes of pyridylureas, less is more. A role for shape complementarity and CH⋯O interactions?",

abstract = "A pyridylurea·tetraazaanthracenedione complex with three hydrogen bonds is more stable than an analogous complex with four hydrogen bonds. An X-ray analysis and modeling suggests a steric mismatch destabilizing the latter and a CH⋯O contact enhancing the stability of the former.",

author = "Quinn, {Jordan R.} and Zimmerman, {Steven C.}",

year = "2004",

month = may,

day = "13",

doi = "10.1021/ol0495016",

language = "English (US)",

volume = "6",

pages = "1649--1652",

journal = "Organic Letters",

issn = "1523-7060",