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The competition between halogen bonds (Br???O) and C–H???O hydrogen bonds: the structure of the acetone–bromine complex revisited

The competition between halogen bonds (Br???O) and C–H???O hydrogen bonds: the structure of the acetone–bromine complex revisited
The competition between halogen bonds (Br???O) and C–H???O hydrogen bonds: the structure of the acetone–bromine complex revisited
A combination of single-crystal X-ray (at 110 and 200 K) and high-resolution neutron powder diffraction (110 K only) using perdeuterated samples has been used to re-determine the crystal structure of the well-known acetone-Br-2 complex. The results indicate a significant interaction between the carbonyl oxygen and the nearest Br atom leading to a marked elongation of the molecular Br-Br bond. In the earlier widely cited crystal structure, no such elongation was reported. Furthermore, the new structure indicates the presence of additional weaker C-H???O and C-H???Br interactions. In this simple complex, in which the halogen bonding is strong compared to the hydrogen bonding (C-H???O), the former interaction is found to occur close (similar to 12 degrees) to the plane of the carbonyl group, with the C-H???Br complementing the stronger halogen bond.
1466-8033
8572-8577
Jones, R.H.
89bf80a4-08a1-4aa3-bca1-331925291fe6
Knight, K.S.
e25bb70a-55c5-471c-8c90-079309411d9f
Marshall, W.G.
c2772eb0-5aa1-491d-9e14-56a29a476b8d
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Pitak, M.B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Jones, R.H.
89bf80a4-08a1-4aa3-bca1-331925291fe6
Knight, K.S.
e25bb70a-55c5-471c-8c90-079309411d9f
Marshall, W.G.
c2772eb0-5aa1-491d-9e14-56a29a476b8d
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Pitak, M.B.
eeb6a00f-2291-4376-830f-d30dfd607ed1

Jones, R.H., Knight, K.S., Marshall, W.G., Coles, Simon J., Horton, Peter N. and Pitak, M.B. (2013) The competition between halogen bonds (Br???O) and C–H???O hydrogen bonds: the structure of the acetone–bromine complex revisited. CrystEngComm, 15 (42), 8572-8577. (doi:10.1039/C3CE41472H).

Record type: Article

Abstract

A combination of single-crystal X-ray (at 110 and 200 K) and high-resolution neutron powder diffraction (110 K only) using perdeuterated samples has been used to re-determine the crystal structure of the well-known acetone-Br-2 complex. The results indicate a significant interaction between the carbonyl oxygen and the nearest Br atom leading to a marked elongation of the molecular Br-Br bond. In the earlier widely cited crystal structure, no such elongation was reported. Furthermore, the new structure indicates the presence of additional weaker C-H???O and C-H???Br interactions. In this simple complex, in which the halogen bonding is strong compared to the hydrogen bonding (C-H???O), the former interaction is found to occur close (similar to 12 degrees) to the plane of the carbonyl group, with the C-H???Br complementing the stronger halogen bond.

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More information

e-pub ahead of print date: 6 September 2013
Published date: 14 November 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 362512
URI: http://eprints.soton.ac.uk/id/eprint/362512
ISSN: 1466-8033
PURE UUID: 8c4d90cd-fceb-43a4-9c04-963782af0862
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016
ORCID for M.B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100

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Date deposited: 26 Feb 2014 12:33
Last modified: 18 Feb 2021 16:54

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Contributors

Author: R.H. Jones
Author: K.S. Knight
Author: W.G. Marshall
Author: Simon J. Coles ORCID iD
Author: Peter N. Horton ORCID iD
Author: M.B. Pitak ORCID iD

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