The structures of uncommon cationic N-alkenyl purine and pyrimidine bases

Gabriele Kociok-Kohn, Kieran C. Molloy, Gareth J. Price, Douglas R. G. Smith

Research output: Contribution to journalArticle

Abstract

The structures of 1,3 bis-(allyl)cytosinium bromide (1), 7,9 bis-(allyl)adeninium bromide hydrate (2) and 3-(butenyl)adeninium bromide (3) have been determined. 1 is dimeric via N-H...Br hydrogen bonds, which further associate into ribbons via weaker C-H...Br interactions. 2 is also dimeric, now from N-H...N hydrogen bonds, which build up further through a complex array of hydrogen bonds involving both the anion and water of crystallization (O-H...N, O-H...Br, C-H...Br). 3 does not dimerise but forms polymeric sheets via a series of N-H...N, C-H...N and C-H...Br hydrogen bonds.

Original languageEnglish
JournalJournal of Heterocyclic Chemistry
Volume53
Issue number1
Early online date22 Dec 2014
DOIs
Publication statusPublished - 26 Jan 2016

Fingerprint

Hydrogen bonds
Bromides
Crystallization
Hydrates
Anions
purine
pyrimidine
Water

Cite this

The structures of uncommon cationic N-alkenyl purine and pyrimidine bases. / Kociok-Kohn, Gabriele; Molloy, Kieran C.; Price, Gareth J.; Smith, Douglas R. G.

In: Journal of Heterocyclic Chemistry, Vol. 53, No. 1, 26.01.2016.

Research output: Contribution to journalArticle

@article{dca83865be2f4a20bb65244a0d8b4899,
title = "The structures of uncommon cationic N-alkenyl purine and pyrimidine bases",
abstract = "The structures of 1,3 bis-(allyl)cytosinium bromide (1), 7,9 bis-(allyl)adeninium bromide hydrate (2) and 3-(butenyl)adeninium bromide (3) have been determined. 1 is dimeric via N-H...Br hydrogen bonds, which further associate into ribbons via weaker C-H...Br interactions. 2 is also dimeric, now from N-H...N hydrogen bonds, which build up further through a complex array of hydrogen bonds involving both the anion and water of crystallization (O-H...N, O-H...Br, C-H...Br). 3 does not dimerise but forms polymeric sheets via a series of N-H...N, C-H...N and C-H...Br hydrogen bonds.",
author = "Gabriele Kociok-Kohn and Molloy, {Kieran C.} and Price, {Gareth J.} and Smith, {Douglas R. G.}",
year = "2016",
month = "1",
day = "26",
doi = "10.1002/jhet.2300",
language = "English",
volume = "53",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "1",

}

TY - JOUR

T1 - The structures of uncommon cationic N-alkenyl purine and pyrimidine bases

AU - Kociok-Kohn, Gabriele

AU - Molloy, Kieran C.

AU - Price, Gareth J.

AU - Smith, Douglas R. G.

PY - 2016/1/26

Y1 - 2016/1/26

N2 - The structures of 1,3 bis-(allyl)cytosinium bromide (1), 7,9 bis-(allyl)adeninium bromide hydrate (2) and 3-(butenyl)adeninium bromide (3) have been determined. 1 is dimeric via N-H...Br hydrogen bonds, which further associate into ribbons via weaker C-H...Br interactions. 2 is also dimeric, now from N-H...N hydrogen bonds, which build up further through a complex array of hydrogen bonds involving both the anion and water of crystallization (O-H...N, O-H...Br, C-H...Br). 3 does not dimerise but forms polymeric sheets via a series of N-H...N, C-H...N and C-H...Br hydrogen bonds.

AB - The structures of 1,3 bis-(allyl)cytosinium bromide (1), 7,9 bis-(allyl)adeninium bromide hydrate (2) and 3-(butenyl)adeninium bromide (3) have been determined. 1 is dimeric via N-H...Br hydrogen bonds, which further associate into ribbons via weaker C-H...Br interactions. 2 is also dimeric, now from N-H...N hydrogen bonds, which build up further through a complex array of hydrogen bonds involving both the anion and water of crystallization (O-H...N, O-H...Br, C-H...Br). 3 does not dimerise but forms polymeric sheets via a series of N-H...N, C-H...N and C-H...Br hydrogen bonds.

UR - http://www.scopus.com/inward/record.url?scp=84920026093&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1002/jhet.2300

U2 - 10.1002/jhet.2300

DO - 10.1002/jhet.2300

M3 - Article

VL - 53

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 1

ER -