Branched Alkanes Have Contrasting Stabilities

Bond separation reactions of highly branched alkanes are used to assess (de)stabilizing interactions associated with various 1,3-nonbonded substituent patterns. While n- and singly methylated alkanes show positive bond separation energies (BSEs), which increase systematically along the series, permethylated alkanes are characterized by decreasing BSEs. Analysis shows that singly methylated alkanes are more stabilized than linear alkane chains and that the unique destabilizing feature of permethylated alkanes arises from the close proximity of bulky methyl groups causing highly distorted geometries along the carbon backbone.


Published in:
Organic Letters, 12, 13, 3070-3073
Year:
2010
Publisher:
American Chemical Society
ISSN:
1523-7060
Keywords:
Laboratories:




 Record created 2010-05-27, last modified 2018-04-09


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)