St Andrews Research Repository

St Andrews University Home
View Item 
  •   St Andrews Research Repository
  • University of St Andrews Research
  • University of St Andrews Research
  • University of St Andrews Research
  • View Item
  •   St Andrews Research Repository
  • University of St Andrews Research
  • University of St Andrews Research
  • University of St Andrews Research
  • View Item
  •   St Andrews Research Repository
  • University of St Andrews Research
  • University of St Andrews Research
  • University of St Andrews Research
  • View Item
  • Login
JavaScript is disabled for your browser. Some features of this site may not work without it.

The difluoromethylene (CF2) group in aliphatic chains : synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups

Thumbnail
View/Open
OHagen_2014_BJOC_TheDifluoromethylene_supplement.pdf (4.789Mb)
OHagen_2014_BJOC_TheDifluoromethylene.pdf (1.753Mb)
Date
06/01/2014
Author
Wang, Yi
Callejo, Ricardo
Slawin, Alexandra M. Z.
O'Hagan, David
Keywords
Difluoromethylene
Fatty acids
Fluorination
Organic fluorine chemistry
Organo-fluorine
Palmitic acid
C-F Bbond
Organofluorine chemistry
Organic-compounds
Flourine
Derivatives
Reagents
QD Chemistry
Metadata
Show full item record
Abstract
The syntheses of palmitic acids and a nonadecane are reported with CF2 groups located 1,3 or 1,4 to each other along the aliphatic chain. Specifically 8,8,10,10- and 8,8,11,11-tetrafluorohexadecanoic acids (6b and 6c) are prepared as well as the singly modified analogue 8,8-difluorohexadecanoic acid (6a). Also 8,8,11,11-tetrafluorononadecane (27) is prepared as a pure hydrocarbon containing a 1,4-di-CF2 motif. The modified palmitic acids are characterized by differential scanning calorimetry (DSC) to determine melting points and phase behaviour relative to palmitic acid (62.5 degrees C). It emerges that 6c, with the CF2 groups placed 1,4- to each other, has a significantly higher melting point (89.9 degrees C) when compared to the other analogues and palmitic acid itself. It is a crystalline compound and the structure reveals an extended anti-zig-zag chain. Similarly 8,8,11,11-tetrafluorononadecane (27) adopts an extended anti-zig-zag structure. This is rationalized by dipolar relaxation between the two CF2 groups placed 1,4 to each other in the extended anti-zig-zag chain and suggests a design modification for long chain aliphatics which can introduce conformational stability.
Citation
Wang , Y , Callejo , R , Slawin , A M Z & O'Hagan , D 2014 , ' The difluoromethylene (CF 2 ) group in aliphatic chains : synthesis and conformational preference of palmitic acids and nonadecane containing CF 2 groups ' , Beilstein Journal of Organic Chemistry , vol. 10 , pp. 18-25 . https://doi.org/10.3762/bjoc.10.4
Publication
Beilstein Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.3762/bjoc.10.4
ISSN
1860-5397
Type
Journal article
Rights
© 2014 Wang et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
 
© 2014 Wang et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
Description
Funding: ERC Advanced Investigator Grant (D.O'H).
Collections
  • University of St Andrews Research
URL
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-10-4
URI
http://hdl.handle.net/10023/4990

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

Advanced Search

Browse

All of RepositoryCommunities & CollectionsBy Issue DateNamesTitlesSubjectsClassificationTypeFunderThis CollectionBy Issue DateNamesTitlesSubjectsClassificationTypeFunder

My Account

Login

Open Access

To find out how you can benefit from open access to research, see our library web pages and Open Access blog. For open access help contact: openaccess@st-andrews.ac.uk.

Accessibility

Read our Accessibility statement.

How to submit research papers

The full text of research papers can be submitted to the repository via Pure, the University's research information system. For help see our guide: How to deposit in Pure.

Electronic thesis deposit

Help with deposit.

Repository help

For repository help contact: Digital-Repository@st-andrews.ac.uk.

Give Feedback

Cookie policy

This site may use cookies. Please see Terms and Conditions.

Usage statistics

COUNTER-compliant statistics on downloads from the repository are available from the IRUS-UK Service. Contact us for information.

© University of St Andrews Library

University of St Andrews is a charity registered in Scotland, No SC013532.

  • Facebook
  • Twitter