The combination of amino acids in their deprotonated and thus anionic form with a choline cation gives origin to a new and potentially important class of organic ionic compounds. A series of such neutral ion pairs has been investigated by first principle methods. The results reveal intriguing structural motives as well as regular patterns in the charge distribution and predict a number of vibrational and optical properties that could guide the experimental investigation of these compounds. The replacement of choline with its phosphocholine analogue causes the spontaneous reciprocal neutralization of cations and anions, taking place through the transfer of a proton between the two ions. Systems of this kind, therefore, provide a wide and easily accessible playground to probe the ionic/polar transition in organic systems, while the easy transfer of H+ among neutral and ionic species points to their potential application as proton conductors. The analysis of the ab initio data highlights similarities as well as discrepancies from the rigid-ions force-field picture and suggests directions for the improvement of empirical models.

Benedetto, A., Bodo, E., Gontrani, L., Ballone, P., Caminiti, R. (2014). Amino Acid Anions in Organic Ionic Compounds. An ab Initio Study of Selected Ion Pairs. JOURNAL OF PHYSICAL CHEMISTRY. B, CONDENSED MATTER, MATERIALS, SURFACES, INTERFACES & BIOPHYSICAL, 118(9), 2471-2486 [10.1021/jp412281n].

Amino Acid Anions in Organic Ionic Compounds. An ab Initio Study of Selected Ion Pairs

Gontrani, L.
Investigation
;
2014-01-01

Abstract

The combination of amino acids in their deprotonated and thus anionic form with a choline cation gives origin to a new and potentially important class of organic ionic compounds. A series of such neutral ion pairs has been investigated by first principle methods. The results reveal intriguing structural motives as well as regular patterns in the charge distribution and predict a number of vibrational and optical properties that could guide the experimental investigation of these compounds. The replacement of choline with its phosphocholine analogue causes the spontaneous reciprocal neutralization of cations and anions, taking place through the transfer of a proton between the two ions. Systems of this kind, therefore, provide a wide and easily accessible playground to probe the ionic/polar transition in organic systems, while the easy transfer of H+ among neutral and ionic species points to their potential application as proton conductors. The analysis of the ab initio data highlights similarities as well as discrepancies from the rigid-ions force-field picture and suggests directions for the improvement of empirical models.
2014
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/02 - CHIMICA FISICA
English
Con Impact Factor ISI
Benedetto, A., Bodo, E., Gontrani, L., Ballone, P., Caminiti, R. (2014). Amino Acid Anions in Organic Ionic Compounds. An ab Initio Study of Selected Ion Pairs. JOURNAL OF PHYSICAL CHEMISTRY. B, CONDENSED MATTER, MATERIALS, SURFACES, INTERFACES & BIOPHYSICAL, 118(9), 2471-2486 [10.1021/jp412281n].
Benedetto, A; Bodo, E; Gontrani, L; Ballone, P; Caminiti, R
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/294544
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