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The singular gas-phase structure of 1-aminocyclopropanecarboxylic acid (Ac3c)

AuthorsJiménez, Ana I. ; Cativiela, Carlos
Issue Date2011
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 133(27): 10621-10628 (2011)
AbstractThe natural nonproteinogenic α-amino acid 1- aminocyclopropanecarboxylic acid (Ac3c) has been vaporized by laser ablation and studied in the gas phase by molecular-beam Fourier transform microwave spectroscopy. Comparison of the experimental rotational and 14N nuclear quadrupole coupling constants with the values predicted ab initio for these parameters has allowed the unambiguous identification of three Ac3c conformers differing in the hydrogen bonding pattern. Two of them resemble those characterized before for the coded aliphatic α-amino acids. Remarkably, a third conformer predicted to be energetically accessible for all of these amino acids but never observed (the so-called missing conformer) has been found for Ac3c, close in energy to the global minimum. This is the first time that such a conformer, stabilized by an N-H ⋯O(H) hydrogen bond, is detected in the rotational spectrum of a gaseous α-amino acid with a nonpolar side chain. The conjugative interaction established between the cyclopropane ring and the adjacent carbonyl group seems to be responsible for the unique conformational properties exhibited by Ac3c. © 2011 American Chemical Society.
Identifiersdoi: 10.1021/ja2033603
issn: 0002-7863
e-issn: 1520-5126
Appears in Collections:(ISQCH) Artículos
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