TY - JOUR
T1 - Hydrogen-bonded chains formed by 5,5-diethylbarbituric acid and bipyridyl tectons
AU - Golden, Emma
AU - Argent, Stephen P.
AU - Blake, Alexander J.
AU - Thebault, Frederic
AU - Champness, Neil R.
PY - 2012/1/19
Y1 - 2012/1/19
N2 - Supramolecular interactions play an important role in determining the solid-state structures of many molecular species. In this study, we describe the role of pyridyl-based molecules in forming hydrogen-bonded chains with 5,5-diethylbarbituric acid (DEB). The single crystal X-ray structures of three hydrogen-bonded co-crystals all exhibit one-dimensional chains formed via N–H…N interactions between pyridyl hydrogen bond acceptors and N–H hydrogen bond donors of DEB. Subtle differences are observed between the three related co-crystals. Although both DEB·4,4’-bipy, 1, and DEB·diaz, 2, (diaz = 2,7-diazapyrene) adopt similar one-dimensional chains with a 1:1 DEB:bipyridyl stoichiometry, π–π interactions play a significant role in the solid-state arrangement of 2 only. In 2(DEB)·dpb, 3, (dpb = 1,4-bis(4-pyridyl)-benzene), an alternative 2:1 DEB:bipyridyl stoichiometry is observed. Dimeric DEB hydrogen-bonded units are linked into hydrogen-bonded chains through further hydrogen bonding. The co-crystal DEB·pypm, 4, (pypm = 5-(4-pyridyl)pyrimidine), also forms dimeric DEB hydrogen-bonded units which interact with the pyridyl groups of pypm. However, the pyrimidine groups of pypm do not participate in hydrogen bonding to DEB molecules and as a result discrete dimeric 2(DEB)·2(pypm) units are formed.
AB - Supramolecular interactions play an important role in determining the solid-state structures of many molecular species. In this study, we describe the role of pyridyl-based molecules in forming hydrogen-bonded chains with 5,5-diethylbarbituric acid (DEB). The single crystal X-ray structures of three hydrogen-bonded co-crystals all exhibit one-dimensional chains formed via N–H…N interactions between pyridyl hydrogen bond acceptors and N–H hydrogen bond donors of DEB. Subtle differences are observed between the three related co-crystals. Although both DEB·4,4’-bipy, 1, and DEB·diaz, 2, (diaz = 2,7-diazapyrene) adopt similar one-dimensional chains with a 1:1 DEB:bipyridyl stoichiometry, π–π interactions play a significant role in the solid-state arrangement of 2 only. In 2(DEB)·dpb, 3, (dpb = 1,4-bis(4-pyridyl)-benzene), an alternative 2:1 DEB:bipyridyl stoichiometry is observed. Dimeric DEB hydrogen-bonded units are linked into hydrogen-bonded chains through further hydrogen bonding. The co-crystal DEB·pypm, 4, (pypm = 5-(4-pyridyl)pyrimidine), also forms dimeric DEB hydrogen-bonded units which interact with the pyridyl groups of pypm. However, the pyrimidine groups of pypm do not participate in hydrogen bonding to DEB molecules and as a result discrete dimeric 2(DEB)·2(pypm) units are formed.
UR - http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000303569300006&KeyUID=WOS:000303569300006
U2 - 10.1080/10610278.2011.622383
DO - 10.1080/10610278.2011.622383
M3 - Article
SN - 1061-0278
VL - 24
SP - 40
EP - 47
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
IS - 1
ER -