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 sub(2) complex. The results indicate a significant interaction between the...
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Published in | CrystEngComm Vol. 15; no. 42; pp. 8572 - 8577 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
01.10.2013
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Subjects | |
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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 sub(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 (~12 degree ) to the plane of the carbonyl group, with the C-H...Br complementing the stronger halogen bond. |
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AbstractList | 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 sub(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 (~12 degree ) to the plane of the carbonyl group, with the C-H...Br complementing the stronger halogen bond. |
Author | Knight, K S Horton, P N Jones, R H Marshall, W G Coles, S J Pitak, M B |
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SubjectTerms | Bonding Crystal structure Diffraction Elongation Halogens Hydrogen bonding Hydrogen bonds X-rays |
Title | The competition between halogen bonds (Br...O) and C-H...O hydrogen bonds: the structure of the acetone-bromine complex revisited |
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