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Crystals 2016, 6(4), 34;

Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings

Department of Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia
ICTM, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia
Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar
Author to whom correspondence should be addressed.
Academic Editor: Sławomir J. Grabowski
Received: 29 January 2016 / Revised: 12 March 2016 / Accepted: 17 March 2016 / Published: 31 March 2016
(This article belongs to the Special Issue Analysis of Hydrogen Bonds in Crystals)
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Saturated acyclic four-atom groups closed with a classic intramolecular hydrogen bond, generating planar five-membered rings (hydrogen-bridged quasi-rings), in which at least one of the ring atoms is bonded to other non-ring atoms that are not in the ring plane and, thus, capable to form intermolecular interactions, were studied in this work, in order to find the preferred mutual positions of these species in crystals and evaluate strength of intermolecular interactions. We studied parallel interactions of these rings by analysing crystal structures in the Cambridge Structural Database (CSD) and by quantum chemical calculations. The rings can have one hydrogen atom out of the ring plane that can form hydrogen bonds between two parallel rings. Hence, in these systems with parallel rings, two types of hydrogen bonds can be present, one in the ring, and the other one between two parallel rings. The CSD search showed that 27% of the rings in the crystal structures form parallel interactions. The calculations at very accurate CCSD(T)/CBS level revealed strong interactions, in model systems of thiosemicarbazide, semicarbazide and glycolamide dimers the energies are −9.68, −7.12 and −4.25 kcal/mol. The hydrogen bonds between rings, as well as dispersion interactions contribute to the strong interaction energies. View Full-Text
Keywords: hydrogen-bridged rings; hydrogen bonds; stacking hydrogen-bridged rings; hydrogen bonds; stacking

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Blagojević, J.P.; Janjić, G.V.; Zarić, S.D. Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings. Crystals 2016, 6, 34.

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