Issue 59, 2003
From the journal:

CrystEngComm

Competitive N–H⋯O[double bond, length half m-dash]C and N–H⋯S[double bond, length half m-dash]C hydrogen bonding in alanine dithiocarbamates

Kraig A. Wheeler,*a   Beverly Harrington,a   Matthew Zappa  and  Endia Caseya  

* Corresponding authors

a Delaware State University, Department of Chemistry, Dover, Delaware, USA
E-mail: kwheeler@dsc.edu
Fax: 302-857-6539
Tel: 302 857 6537

Abstract

The crystal structures of a homologous family of alanine-based dithiocarbamates reveal structural patterns influenced by intermolecular O–H⋯O, N–H⋯O and N–H⋯S interactions. These chemical systems differ by the steric properties of the pendent alkyl groups (i.e., methyl, ethyl, isopropyl and benzyl). Although a carboxylic acid head-to-head dimer provides a common theme for these structures, variations in molecular alignment arise from the use of the dithiocarbamate N–H donor group in either N–H⋯O[double bond, length half m-dash]C or N–H⋯S[double bond, length half m-dash]C interactions. The molecular features and crystal structure patterns responsible for the competitive self-assembly provide the basis of discussion.

Graphical abstract: Competitive N–H⋯O [[double bond, length half m-dash]] C and N–H⋯S [[double bond, length half m-dash]] C hydrogen bonding in alanine dithiocarbamates

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Article information

DOI
https://doi.org/10.1039/B308330F
Article type
Paper
Submitted
21 Jul 2003
Accepted
20 Aug 2003
First published
03 Sep 2003

CrystEngComm, 2003,5, 337-342

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Competitive N–H⋯O[double bond, length half m-dash]C and N–H⋯S[double bond, length half m-dash]C hydrogen bonding in alanine dithiocarbamates

K. A. Wheeler, B. Harrington, M. Zapp and E. Casey, CrystEngComm, 2003, 5, 337 DOI: 10.1039/B308330F

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