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Does intermolecular S=O?H–C–S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?

Does intermolecular S=O?H–C–S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?
Does intermolecular S=O?H–C–S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?
Hydrogen bonding between the sulfur oxygens and the acidic alpha-hydrogens in sulfoxides and sulfones is proposed as a supramolecular synthon in crystal engineering. A systematic analysis of supramolecular interactions in the solid state of a series of structurally related aryl benzyl sulfides, sulfoxides and sulfones was undertaken to establish the extent to which such hydrogen bonds persist as a structure determining feature in the solid state. The impact of the level of oxidation at sulfur, steric and electronic effects of substituents on the aryl rings and methyl substitution a to the sulfur functional group on the solid state structure of the compounds have been explored. The impact of stereochemical features, including relative and absolute stereochemistry, is also discussed.
1466-8033
2910-2927
Brondel, Nicolas
41ee648d-0b35-4c43-b944-ce872e02eb12
Moynihan, Eamonn J.A.
b252c0f7-fd8e-4485-ab97-b74131775dbd
Lehane, K. Niamh
90978607-960f-45a9-9b9d-e4a95edf0b59
Eccles, Kevin S.
8e77a90b-b39b-49d8-ae48-42f8573fb242
Elcoate, Curtis J.
0add4d25-8027-46ef-a208-61be1b660eaa
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lawrence, Simon E.
9f9d8451-35de-4ee7-8c47-ed6e84748b56
Maguire, Anita R.
b537ff7f-46fe-43bf-8194-3162ab7d94eb
Brondel, Nicolas
41ee648d-0b35-4c43-b944-ce872e02eb12
Moynihan, Eamonn J.A.
b252c0f7-fd8e-4485-ab97-b74131775dbd
Lehane, K. Niamh
90978607-960f-45a9-9b9d-e4a95edf0b59
Eccles, Kevin S.
8e77a90b-b39b-49d8-ae48-42f8573fb242
Elcoate, Curtis J.
0add4d25-8027-46ef-a208-61be1b660eaa
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lawrence, Simon E.
9f9d8451-35de-4ee7-8c47-ed6e84748b56
Maguire, Anita R.
b537ff7f-46fe-43bf-8194-3162ab7d94eb

Brondel, Nicolas, Moynihan, Eamonn J.A., Lehane, K. Niamh, Eccles, Kevin S., Elcoate, Curtis J., Coles, Simon J., Lawrence, Simon E. and Maguire, Anita R. (2010) Does intermolecular S=O?H–C–S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state? CrystEngComm, 12 (10), 2910-2927. (doi:10.1039/c000371a).

Record type: Article

Abstract

Hydrogen bonding between the sulfur oxygens and the acidic alpha-hydrogens in sulfoxides and sulfones is proposed as a supramolecular synthon in crystal engineering. A systematic analysis of supramolecular interactions in the solid state of a series of structurally related aryl benzyl sulfides, sulfoxides and sulfones was undertaken to establish the extent to which such hydrogen bonds persist as a structure determining feature in the solid state. The impact of the level of oxidation at sulfur, steric and electronic effects of substituents on the aryl rings and methyl substitution a to the sulfur functional group on the solid state structure of the compounds have been explored. The impact of stereochemical features, including relative and absolute stereochemistry, is also discussed.

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e-pub ahead of print date: 11 May 2010
Published date: 2010
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 346193
URI: http://eprints.soton.ac.uk/id/eprint/346193
ISSN: 1466-8033
PURE UUID: a5464785-4e2e-41fc-a882-33365c53baef
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 17 Dec 2012 10:42
Last modified: 07 Oct 2020 07:32

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