The University of Southampton
University of Southampton Institutional Repository

The solid-state packing of sulfur substituted 2-aminopyrimidines and the occurrence of N-H—S hydrogen-bonding associations

The solid-state packing of sulfur substituted 2-aminopyrimidines and the occurrence of N-H—S hydrogen-bonding associations
The solid-state packing of sulfur substituted 2-aminopyrimidines and the occurrence of N-H—S hydrogen-bonding associations
The solid-state packing arrays of eight 4-sulfur substituted 2-aminopyrimidines have been examined and the occurrence of N–H—S hydrogen-bonding associations in those structures discussed. The eight compounds were 2,5-diamino-4-mercapto-6-methylpyrimidine 1, 2-amino-4,6-bis(phenylthio)pyrimidine 2, 2-amino-4,6-bis(4-chlorophenylthio)pyrimidine 3, 2-amino-4,6-bis(4-methylphenylthio)pyrimidine 4, 5 (two polymorphs), 2-amino-4-chloro-6-(4-fluorophenylthio)pyrimidine 6, 2-amino-4-(4-chlorophenylthio)-6-morpholinopyrimidine 7, 2-amino-4-(4-(2,3-dimethylphenyl)piperizino)-6-phenylthiopyrimidine 8, and 2-amino-4-(4-(2-ethoxyphenyl)piperizino)-6-(4-chlorophenylthio)pyrimidine 9. The single-crystal x-ray structures of 1 – 3 have been previously reported while the structures of 4 – 9 are presented in this paper. All packing motifs exhibit characteristic R(2)2(8) hydrogen-bonded 2-aminopyrimidine dimers, to varying degrees of polymerisation, whereas compounds 1 – 5 and 7 include N–H—S associations, the majority of which are three-center associations with an included N–H—N interaction.
2-aminopyrimidine, hydrogen bond, x-ray crystal structure acid, cocrystal
79-94
Lynch, Daniel E.
edff6860-7481-48b9-ac5a-25a7fd23efdd
McClenaghan, Ian
85f27d63-60d4-4d37-96db-1c8fe67d4fcc
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lynch, Daniel E.
edff6860-7481-48b9-ac5a-25a7fd23efdd
McClenaghan, Ian
85f27d63-60d4-4d37-96db-1c8fe67d4fcc
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8

Lynch, Daniel E., McClenaghan, Ian, Light, Mark E. and Coles, Simon J. (2002) The solid-state packing of sulfur substituted 2-aminopyrimidines and the occurrence of N-H—S hydrogen-bonding associations. Crystal Engineering, 5 (1), 79-94. (doi:10.1016/S1463-0184(02)00007-2).

Record type: Article

Abstract

The solid-state packing arrays of eight 4-sulfur substituted 2-aminopyrimidines have been examined and the occurrence of N–H—S hydrogen-bonding associations in those structures discussed. The eight compounds were 2,5-diamino-4-mercapto-6-methylpyrimidine 1, 2-amino-4,6-bis(phenylthio)pyrimidine 2, 2-amino-4,6-bis(4-chlorophenylthio)pyrimidine 3, 2-amino-4,6-bis(4-methylphenylthio)pyrimidine 4, 5 (two polymorphs), 2-amino-4-chloro-6-(4-fluorophenylthio)pyrimidine 6, 2-amino-4-(4-chlorophenylthio)-6-morpholinopyrimidine 7, 2-amino-4-(4-(2,3-dimethylphenyl)piperizino)-6-phenylthiopyrimidine 8, and 2-amino-4-(4-(2-ethoxyphenyl)piperizino)-6-(4-chlorophenylthio)pyrimidine 9. The single-crystal x-ray structures of 1 – 3 have been previously reported while the structures of 4 – 9 are presented in this paper. All packing motifs exhibit characteristic R(2)2(8) hydrogen-bonded 2-aminopyrimidine dimers, to varying degrees of polymerisation, whereas compounds 1 – 5 and 7 include N–H—S associations, the majority of which are three-center associations with an included N–H—N interaction.

This record has no associated files available for download.

More information

Published date: 2002
Keywords: 2-aminopyrimidine, hydrogen bond, x-ray crystal structure acid, cocrystal

Identifiers

Local EPrints ID: 19815
URI: http://eprints.soton.ac.uk/id/eprint/19815
PURE UUID: 88055e56-160c-4caf-a4e3-4ebd396b5cf8
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 21 Feb 2006
Last modified: 08 Jan 2022 02:50

Export record

Altmetrics

Contributors

Author: Daniel E. Lynch
Author: Ian McClenaghan
Author: Mark E. Light ORCID iD
Author: Simon J. Coles ORCID iD

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×