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Rondino F, Satta M, Piccirillo S, et al. Chlorine Para-Substitution of 1-Phenylethanol: Resonant Photoionization Spectroscopy and Quantum Chemical Calculations of Hydrated and Diastereomeric Complexes. J Phys Chem A. 2016;120(27):5023-31doi: 10.1021/acs.jpca.5b12746.
Rondino, F., Satta, M., Piccirillo, S., Ciavardini, A., Giardini, A., Speranza, M., Avaldi, L., & Paladini, A. (2016). Chlorine Para-Substitution of 1-Phenylethanol: Resonant Photoionization Spectroscopy and Quantum Chemical Calculations of Hydrated and Diastereomeric Complexes. The journal of physical chemistry. A, 120(27), 5023-31. https://doi.org/10.1021/acs.jpca.5b12746
Rondino, Flaminia, et al. "Chlorine Para-Substitution of 1-Phenylethanol: Resonant Photoionization Spectroscopy and Quantum Chemical Calculations of Hydrated and Diastereomeric Complexes." The journal of physical chemistry. A vol. 120,27 (2016): 5023-31. doi: https://doi.org/10.1021/acs.jpca.5b12746
Rondino F, Satta M, Piccirillo S, Ciavardini A, Giardini A, Speranza M, Avaldi L, Paladini A. Chlorine Para-Substitution of 1-Phenylethanol: Resonant Photoionization Spectroscopy and Quantum Chemical Calculations of Hydrated and Diastereomeric Complexes. J Phys Chem A. 2016 Jul 14;120(27):5023-31. doi: 10.1021/acs.jpca.5b12746. Epub 2016 May 11. PMID: 27144968.
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J Phys Chem A. 2016 Jul 14;120(27):5023-31. doi: 10.1021/acs.jpca.5b12746. Epub 2016 May 11.

Chlorine Para-Substitution of 1-Phenylethanol: Resonant Photoionization Spectroscopy and Quantum Chemical Calculations of Hydrated and Diastereomeric Complexes.

The journal of physical chemistry. A

Flaminia Rondino, Mauro Satta, Susanna Piccirillo, Alessandra Ciavardini, Anna Giardini, Maurizio Speranza, Lorenzo Avaldi, Alessandra Paladini

Affiliations

  1. Dip.to di Chimica e Tecnologie del Farmaco, Università degli Studi di Roma La Sapienza , p.le Aldo Moro 5, 00185, Rome, Italy.
  2. CNR-ISMN, c/o Dip.to di Chimica, Università degli Studi di Roma La Sapienza , p.le Aldo Moro 5, 00185, Rome, Italy.
  3. Dip.to di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata" , via della Ricerca Scientifica, 00133 Rome, Italy.
  4. CNR-ISM , Area della Ricerca di Roma 1, via Salaria km 29.300, 00015 Monterotondo (RM), Italy.

PMID: 27144968 DOI: 10.1021/acs.jpca.5b12746

Abstract

The conformational landscape of (S)-1-(4-chlorophenyl)ethanol, its monohydrated complex, and its diastereomeric adducts with R- and S-butan-2-ol, have been investigated by resonant two-photon ionization (R2PI) spectroscopy coupled with time-of-flight mass spectrometry. Theoretical calculations at the D-B3LYP/6-31++G** level of theory have been performed to assist in the interpretation of the spectra and in the assignment of the structures. The R2PI spectra and the predicted structures have been compared with those obtained on the analogous non-halogenated and fluorinated systems, i.e., (R)-1-phenylethanol and (S)-1-(4-fluorophenyl)ethanol, respectively. It appears that the presence of chlorine atom in the para position of the aromatic ring does not influence the overall geometry of bare molecule and its complexes with respect to the non-halogenated analogous systems. Anyway, it affects the electron density in the π system, and in turn the strength of OH···π and CH···π interactions. A spectral chiral discrimination is evident from the R2PI spectra of the diastereomeric adducts of (S)-1-(4-chlorophenyl)ethanol with the two enantiomers of butan-2-ol.

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