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Title: Auto-oligomerization and hydration of pyrrole revealed by x-ray absorption spectroscopy

Abstract

Near edge x-ray absorption fine structure spectra have been measured at the carbon and nitrogen K-edges of the prototypical aromatic molecule, pyrrole, both in the gas phase and when solvated in water, and compared with spectra simulated using a combination of classical molecular dynamics and first principles density functional theory in the excited state core hole approximation. The excellent agreement enabled detailed assignments. Pyrrole is highly reactive, particularly in water, and reaction products formed by the auto-oligomerization of pyrrole are identified. The solvated spectra have been measured at two different temperatures, indicating that the final states remain largely unaffected by both hydration and temperature. This is somewhat unexpected, since the nitrogen in pyrrole can donate a hydrogen bond to water.

Authors:
; ; ; ;  [1];  [2]
  1. Department of Chemistry, University of California, Berkeley, California 94720-1460 (United States) and Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720 (United States)
  2. Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, California 94720 (United States)
Publication Date:
OSTI Identifier:
21559773
Resource Type:
Journal Article
Resource Relation:
Journal Name: Journal of Chemical Physics; Journal Volume: 131; Journal Issue: 11; Other Information: DOI: 10.1063/1.3223539; (c) 2009 American Institute of Physics
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 74 ATOMIC AND MOLECULAR PHYSICS; ABSORPTION; ABSORPTION SPECTROSCOPY; ALLOCATIONS; APPROXIMATIONS; CARBON; DENSITY FUNCTIONAL METHOD; EXCITED STATES; FINE STRUCTURE; HYDRATION; HYDROGEN; MOLECULAR DYNAMICS METHOD; NITROGEN; PYRROLES; SIMULATION; SPECTRA; WATER; X RADIATION; X-RAY SPECTROSCOPY; AZOLES; CALCULATION METHODS; ELECTROMAGNETIC RADIATION; ELEMENTS; ENERGY LEVELS; HETEROCYCLIC COMPOUNDS; HYDROGEN COMPOUNDS; IONIZING RADIATIONS; NONMETALS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; OXYGEN COMPOUNDS; RADIATIONS; SOLVATION; SORPTION; SPECTROSCOPY; VARIATIONAL METHODS

Citation Formats

Schwartz, Craig P., Uejio, Janel S., Duffin, Andrew M., England, Alice H., Saykally, Richard J., and Prendergast, David. Auto-oligomerization and hydration of pyrrole revealed by x-ray absorption spectroscopy. United States: N. p., 2009. Web. doi:10.1063/1.3223539.
Schwartz, Craig P., Uejio, Janel S., Duffin, Andrew M., England, Alice H., Saykally, Richard J., & Prendergast, David. Auto-oligomerization and hydration of pyrrole revealed by x-ray absorption spectroscopy. United States. doi:10.1063/1.3223539.
Schwartz, Craig P., Uejio, Janel S., Duffin, Andrew M., England, Alice H., Saykally, Richard J., and Prendergast, David. Mon . "Auto-oligomerization and hydration of pyrrole revealed by x-ray absorption spectroscopy". United States. doi:10.1063/1.3223539.
@article{osti_21559773,
title = {Auto-oligomerization and hydration of pyrrole revealed by x-ray absorption spectroscopy},
author = {Schwartz, Craig P. and Uejio, Janel S. and Duffin, Andrew M. and England, Alice H. and Saykally, Richard J. and Prendergast, David},
abstractNote = {Near edge x-ray absorption fine structure spectra have been measured at the carbon and nitrogen K-edges of the prototypical aromatic molecule, pyrrole, both in the gas phase and when solvated in water, and compared with spectra simulated using a combination of classical molecular dynamics and first principles density functional theory in the excited state core hole approximation. The excellent agreement enabled detailed assignments. Pyrrole is highly reactive, particularly in water, and reaction products formed by the auto-oligomerization of pyrrole are identified. The solvated spectra have been measured at two different temperatures, indicating that the final states remain largely unaffected by both hydration and temperature. This is somewhat unexpected, since the nitrogen in pyrrole can donate a hydrogen bond to water.},
doi = {10.1063/1.3223539},
journal = {Journal of Chemical Physics},
number = 11,
volume = 131,
place = {United States},
year = {Mon Sep 21 00:00:00 EDT 2009},
month = {Mon Sep 21 00:00:00 EDT 2009}
}