ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The gas-phase basicity (GB) of open-chain and cyclic diols and triols has been determined by the method of dissociation of proton-bound adducts using 1,4-butanediol and cis- and trans-1,3-cyclohexanediol as reference compounds. The GB and proton affinity (PA) of the two cyclic reference diols have been obtained in ion-cyclotron-resonance experiments. The unimolecular and the collision-activated dissociations of the ammonium adducts of the polyols allow a ranking of their GB and PA values which reflects the various structural and stereochemical effects. The possibility of internal H-bonding between the two OH groups leads to a strong increase of the PA values. The incremental effect of chain length on the PA of open-chain diols is evidenced, as well as the detailed influence of the configuration and conformation for cyclopentane- and cyclohexanediols, and -triols. These experiments also emphasized the predominant role of doubly H-bound ammonium/diol chelate conformations as opposed to singly proton-bound species.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680619
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