Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules

Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules

Cocrystals of 5-nitrouracil with solvent molecules, dioxane, pyridine, DMSO, formamide and ethanol as well as with piperazine, N, N'-dimethylpiperazine, 3-aminopyridine and diazabicyclo [2.2.2]octane obtained by deliberate inclusion, have been examined by X-ray crystallography. The tape structu...

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Main Authors: Thomas, Reji, Gopalan, R Srinivasa, Kulkarni, GU, Rao, CNR
Format: Online
Language:English
Published: BioMed Central 2005
Online Access:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399463/
id pubmed-1399463
recordtype oai_dc
spelling pubmed-13994632006-03-13 Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules Thomas, Reji Gopalan, R Srinivasa Kulkarni, GU Rao, CNR Full Research Paper Cocrystals of 5-nitrouracil with solvent molecules, dioxane, pyridine, DMSO, formamide and ethanol as well as with piperazine, N, N'-dimethylpiperazine, 3-aminopyridine and diazabicyclo [2.2.2]octane obtained by deliberate inclusion, have been examined by X-ray crystallography. The tape structure found in the parent centric form of nitrouracil is retained with some modifications in the cocrystals with dioxane, piperazine, diazabicyclo [2.2.2]octane, N,N'-dimethylpiperazine, pyridine and DMSO, with the guest molecules forming alternate tapes. In cocrystals involving formamide, ethanol and 3-aminopyridine, the molecular tapes exhibit mixed compositions. The observed bonding patterns have been classified into six schemes. Interestingly, quadruple type hydrogen bonding patterns are seen in cocrystals containing 3-aminopyridine or ethanol and water, while a network of acyclic tetrahedral pentamers of water is found in the cocrystal containing diazabicyclo [2.2.2]octane and water. BioMed Central 2005-12-09 /pmc/articles/PMC1399463/ /pubmed/16542030 http://dx.doi.org/10.1186/1860-5397-1-15 Text en Copyright © 2005 Thomas et al; licensee Beilstein-Institut. http://creativecommons.org/licenses/by/2.0 This is an Open Access article distributed under the terms of the Creative Commons Attribution License ( (http://creativecommons.org/licenses/by/2.0) ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
repository_type Open Access Journal
institution_category Foreign Institution
institution US National Center for Biotechnology Information
building NCBI PubMed
collection Online Access
language English
format Online
author Thomas, Reji
Gopalan, R Srinivasa
Kulkarni, GU
Rao, CNR
spellingShingle Thomas, Reji
Gopalan, R Srinivasa
Kulkarni, GU
Rao, CNR
Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
author_facet Thomas, Reji
Gopalan, R Srinivasa
Kulkarni, GU
Rao, CNR
author_sort Thomas, Reji
title Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
title_short Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
title_full Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
title_fullStr Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
title_full_unstemmed Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
title_sort hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules
description Cocrystals of 5-nitrouracil with solvent molecules, dioxane, pyridine, DMSO, formamide and ethanol as well as with piperazine, N, N'-dimethylpiperazine, 3-aminopyridine and diazabicyclo [2.2.2]octane obtained by deliberate inclusion, have been examined by X-ray crystallography. The tape structure found in the parent centric form of nitrouracil is retained with some modifications in the cocrystals with dioxane, piperazine, diazabicyclo [2.2.2]octane, N,N'-dimethylpiperazine, pyridine and DMSO, with the guest molecules forming alternate tapes. In cocrystals involving formamide, ethanol and 3-aminopyridine, the molecular tapes exhibit mixed compositions. The observed bonding patterns have been classified into six schemes. Interestingly, quadruple type hydrogen bonding patterns are seen in cocrystals containing 3-aminopyridine or ethanol and water, while a network of acyclic tetrahedral pentamers of water is found in the cocrystal containing diazabicyclo [2.2.2]octane and water.
publisher BioMed Central
publishDate 2005
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399463/
_version_ 1611381209014730752

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