Low-temperature photoelectron spectroscopy of aliphatic dicarboxylate monoanions, HO 2C(CH 2) nCO 2 - (n = 1-10) : Hydrogen bond induced cyclization and strain energies

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Detail(s)

Original languageEnglish
Pages (from-to)7801-7805
Journal / PublicationJournal of Physical Chemistry A
Volume110
Issue number25
Publication statusPublished - 29 Jun 2006
Externally publishedYes

Abstract

Photoelectron spectra of singly charged dicarboxylate anions HO 2C(CH 2) nCO 2 (n = 1-10) are obtained at two different temperatures (300 and 70 K) at 193 nm. The electron binding energies of these species are observed to be much higher than the singly charged monocarboxylate anions, suggesting that the singly charged dicarboxylate anions are cyclic due to strong intramolecular hydrogen bonding between the terminal -CO 2H and -CO 2 - groups. The measured electron binding energies are observed to depend on the chain length, reflecting the different -CO 2H⋯ -O 2C- hydrogen bonding strength as a result of strain in the cyclic conformation. A minimum binding energy is found at n = 5, indicating that its intramolecular hydrogen bond is the weakest. At 70 K, all spectra are blue shifted relative to the room-temperature spectra with the maximum binding energy shift occurring at n = 5. These observations suggest that the cyclic conformation of HO 2C(CH 2) 5CO 2 -(a ten-membered ring) is the most strained among the 10 anions. The present study shows that the -CO 2H⋯ -O 2C-hydorogen bonding strength is different among the 10 anions and it is very sensitive to the strain in the cyclic conformations. © 2006 American Chemical Society.

Citation Format(s)

Low-temperature photoelectron spectroscopy of aliphatic dicarboxylate monoanions, HO 2C(CH 2) nCO 2 - (n = 1-10) : Hydrogen bond induced cyclization and strain energies. / Woo, Hin-Koon; Wang, Xue-Bin; Lau, Kai-Chung et al.

In: Journal of Physical Chemistry A, Vol. 110, No. 25, 29.06.2006, p. 7801-7805.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review