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Molecules 2013, 18(8), 8712-8724;

Halogen Bonding in (Z)-2-Iodocinnamaldehyde

Mahidol University International College, Mahidol University, Salaya Campus, Nakorn Pathom 73170, Thailand
Istituto Chimica Biomolecolare CNR, P.le Aldo Moro 5, Rome 00185, Italy
Department of Chemistry, Vassar College, Poughkeepsie, NY 12604-0484, USA
Author to whom correspondence should be addressed.
Received: 24 May 2013 / Revised: 11 July 2013 / Accepted: 18 July 2013 / Published: 24 July 2013
(This article belongs to the Special Issue Halogen Bond: Application and Prospect)
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Based on the bulkiness of the iodine atom, a non-planar conformation was expected for the title compound. Instead, its molecular structure is planar, as experimentally determined using single crystal X-ray diffraction, and confirmed theoretically by DFT calculations on the single molecule and the halogen pair paired molecules, therefore ruling out crystal packing forces as a principal factor leading to planarity. Indeed, planarity is ascribed to the carbonyl double bond, as when this bond is saturated on forming the related alcohol derivative, the molecule loses planarity. The X-ray molecular structure shows an intermolecular separation between the iodine and the oxygen of the carbonyl shorter than the corresponding van der Waals distance suggesting a weak halogen bond interaction. DFT minimization of this 2-molecule arrangement shows the iodine--oxygen distance much shorter than that observed in the crystal interaction and confirming its stronger halogen bond nature. A trend between increasing I•••O(carbonyl) separation and decreasing C-I•••O(carbonyl) angle is demonstrated, further confirming the existence of a halogen bond. View Full-Text
Keywords: halogen bond; α-iodoenals; crystal structure; DFT halogen bond; α-iodoenals; crystal structure; DFT

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Bovonsombat, P.; Caruso, F.; Jdaydani, A.; Rossi, M. Halogen Bonding in (Z)-2-Iodocinnamaldehyde. Molecules 2013, 18, 8712-8724.

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