Molecules 2013, 18(8), 8712-8724; doi:10.3390/molecules18088712
Article

Halogen Bonding in (Z)-2-Iodocinnamaldehyde

1,* email, 2,3, 3 and 3
Received: 24 May 2013; in revised form: 11 July 2013 / Accepted: 18 July 2013 / Published: 24 July 2013
(This article belongs to the Special Issue Halogen Bond: Application and Prospect)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: halogen bond; α-iodoenals; crystal structure; DFT
PDF Full-text Download PDF Full-Text [511 KB, uploaded 18 June 2014 20:08 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

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

AMA Style

Bovonsombat P, Caruso F, Jdaydani A, Rossi M. Halogen Bonding in (Z)-2-Iodocinnamaldehyde. Molecules. 2013; 18(8):8712-8724.

Chicago/Turabian Style

Bovonsombat, Pakorn; Caruso, Francesco; Jdaydani, Andrew; Rossi, Miriam. 2013. "Halogen Bonding in (Z)-2-Iodocinnamaldehyde." Molecules 18, no. 8: 8712-8724.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert