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Crystals 2016, 6(4), 37; doi:10.3390/cryst6040037

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

1
Département de chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, QC J1E 4K1, Canada
2
Laboratoire de synthèse supramoléculaire, Département de chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e avenue nord, Sherbrooke, QC J1H 5N4, Canada
*
Authors to whom correspondence should be addressed.
Academic Editor: Sławomir J. Grabowski
Received: 4 February 2016 / Revised: 24 March 2016 / Accepted: 24 March 2016 / Published: 2 April 2016
(This article belongs to the Special Issue Analysis of Hydrogen Bonds in Crystals)
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Abstract

Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH2-diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H···O=C) or halogen bond interactions (diyne-Br···O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions. View Full-Text
Keywords: isomorphism; crystal structures; supramolecular sheets; hydrogen bond; halogen bond; synthesis; diacetylene; bromodiyne; terminal alkyne; DFT theoretical calculation isomorphism; crystal structures; supramolecular sheets; hydrogen bond; halogen bond; synthesis; diacetylene; bromodiyne; terminal alkyne; DFT theoretical calculation
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MDPI and ACS Style

Baillargeon, P.; Caron-Duval, É.; Pellerin, É.; Gagné, S.; Dory, Y.L. Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds. Crystals 2016, 6, 37.

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