Investigating the influence of (Deoxy)fluorination on the lipophilicity of non-UV-active fluorinated alkanols and carbohydrates by a new log P determination method
Investigating the influence of (Deoxy)fluorination on the lipophilicity of non-UV-active fluorinated alkanols and carbohydrates by a new log P determination method
Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (log?P) modulation. However, the determination of log?P is cumbersome for non-UV-active compounds. A new variation of the shake-flask log?P determination method is presented, enabling the measurement of log?P for fluorinated compounds with or without UV activity regardless of whether they are hydrophilic or lipophilic. No calibration curves or measurements of compound masses/aliquot volumes are required. With this method, the influence of fluorination on the lipophilicity of fluorinated aliphatic alcohols was determined, and the log?P values of fluorinated carbohydrates were measured. Interesting trends and changes, for example, for the dependence on relative stereochemistry, are reported
fluorinated carbohydrates, fluorine, fluoroalcohols, lipophilicity, NMR spectroscopy
674-678
Linclau, Bruno
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Wang, Zhong
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Compain, Guillaume
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Paumelle, Vincent
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Fontenelle, Clement Q.
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Wells, Neil
86312185-007b-495b-86da-4e2e5b9b8025
Weymouth-Wilson, Alex
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5 January 2016
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Wang, Zhong
fe914552-33f1-4f0a-b8a1-52b82e8cb89e
Compain, Guillaume
8ce9177d-a363-49c5-a51b-af3b4184b8e8
Paumelle, Vincent
ca2d582b-9c1c-4112-98f1-506082f1da92
Fontenelle, Clement Q.
c746c5ea-96bc-46c2-849d-47215ab58c03
Wells, Neil
86312185-007b-495b-86da-4e2e5b9b8025
Weymouth-Wilson, Alex
a25a6ccc-864f-45be-bbd3-016286c5f563
Linclau, Bruno, Wang, Zhong, Compain, Guillaume, Paumelle, Vincent, Fontenelle, Clement Q., Wells, Neil and Weymouth-Wilson, Alex
(2016)
Investigating the influence of (Deoxy)fluorination on the lipophilicity of non-UV-active fluorinated alkanols and carbohydrates by a new log P determination method.
Angewandte Chemie International Edition, 55 (2), .
(doi:10.1002/anie.201509460).
(PMID:26592706)
Abstract
Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (log?P) modulation. However, the determination of log?P is cumbersome for non-UV-active compounds. A new variation of the shake-flask log?P determination method is presented, enabling the measurement of log?P for fluorinated compounds with or without UV activity regardless of whether they are hydrophilic or lipophilic. No calibration curves or measurements of compound masses/aliquot volumes are required. With this method, the influence of fluorination on the lipophilicity of fluorinated aliphatic alcohols was determined, and the log?P values of fluorinated carbohydrates were measured. Interesting trends and changes, for example, for the dependence on relative stereochemistry, are reported
Text
2016_ACE logP.pdf
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e-pub ahead of print date: 23 November 2015
Published date: 5 January 2016
Keywords:
fluorinated carbohydrates, fluorine, fluoroalcohols, lipophilicity, NMR spectroscopy
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 384492
URI: http://eprints.soton.ac.uk/id/eprint/384492
ISSN: 1433-7851
PURE UUID: 06c2cf03-a4f7-4e03-ab7c-e9965dc15655
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Date deposited: 01 Dec 2015 14:59
Last modified: 15 Mar 2024 03:05
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Contributors
Author:
Guillaume Compain
Author:
Vincent Paumelle
Author:
Clement Q. Fontenelle
Author:
Alex Weymouth-Wilson
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