Communication: Remarkable electrophilicity of the oxalic acid monomer: An anion photoelectron spectroscopy and theoretical study

Angela Buonaugurio; Jacob Graham; Allyson Buytendyk; Kit H. Bowen; Matthew R. Ryder; Zibo G. Keolopile; MacIej Haranczyk; MacIej Gutowski

doi:10.1063/1.4882655

Communication: Remarkable electrophilicity of the oxalic acid monomer: An anion photoelectron spectroscopy and theoretical study

Angela Buonaugurio, Jacob Graham, Allyson Buytendyk, Kit H. Bowen, Matthew R. Ryder, Zibo G. Keolopile, MacIej Haranczyk, MacIej Gutowski

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Our experimental and computational results demonstrate an unusual electrophilicity of oxalic acid, the simplest dicarboxylic acid. The monomer is characterized by an adiabatic electron affinity and electron vertical detachment energy of 0.72 and 1.08 eV (±0.05 eV), respectively. The electrophilicity results primarily from the bonding carbon-carbon interaction in the singly occupied molecular orbital of the anion, but it is further enhanced by intramolecular hydrogen bonds. The well-resolved structure in the photoelectron spectrum is reproduced theoretically, based on Franck-Condon factors for the vibronic anion → neutral transitions.

Original language	English
Article number	221103
Journal	Journal of Chemical Physics
Volume	140
Issue number	22
DOIs	https://doi.org/10.1063/1.4882655
State	Published - Jun 14 2014
Externally published	Yes

Access to Document

10.1063/1.4882655

Cite this

@article{bee9f5b7505d4d988619fab8f2a3c44e,

title = "Communication: Remarkable electrophilicity of the oxalic acid monomer: An anion photoelectron spectroscopy and theoretical study",

abstract = "Our experimental and computational results demonstrate an unusual electrophilicity of oxalic acid, the simplest dicarboxylic acid. The monomer is characterized by an adiabatic electron affinity and electron vertical detachment energy of 0.72 and 1.08 eV (±0.05 eV), respectively. The electrophilicity results primarily from the bonding carbon-carbon interaction in the singly occupied molecular orbital of the anion, but it is further enhanced by intramolecular hydrogen bonds. The well-resolved structure in the photoelectron spectrum is reproduced theoretically, based on Franck-Condon factors for the vibronic anion → neutral transitions.",

author = "Angela Buonaugurio and Jacob Graham and Allyson Buytendyk and Bowen, {Kit H.} and Ryder, {Matthew R.} and Keolopile, {Zibo G.} and MacIej Haranczyk and MacIej Gutowski",

year = "2014",

month = jun,

day = "14",

doi = "10.1063/1.4882655",

language = "English",

volume = "140",

journal = "Journal of Chemical Physics",

issn = "0021-9606",

publisher = "American Institute of Physics",

number = "22",

}

TY - JOUR

T1 - Communication

T2 - Remarkable electrophilicity of the oxalic acid monomer: An anion photoelectron spectroscopy and theoretical study

AU - Buonaugurio, Angela

AU - Graham, Jacob

AU - Buytendyk, Allyson

AU - Bowen, Kit H.

AU - Ryder, Matthew R.

AU - Keolopile, Zibo G.

AU - Haranczyk, MacIej

AU - Gutowski, MacIej

PY - 2014/6/14

Y1 - 2014/6/14

N2 - Our experimental and computational results demonstrate an unusual electrophilicity of oxalic acid, the simplest dicarboxylic acid. The monomer is characterized by an adiabatic electron affinity and electron vertical detachment energy of 0.72 and 1.08 eV (±0.05 eV), respectively. The electrophilicity results primarily from the bonding carbon-carbon interaction in the singly occupied molecular orbital of the anion, but it is further enhanced by intramolecular hydrogen bonds. The well-resolved structure in the photoelectron spectrum is reproduced theoretically, based on Franck-Condon factors for the vibronic anion → neutral transitions.

AB - Our experimental and computational results demonstrate an unusual electrophilicity of oxalic acid, the simplest dicarboxylic acid. The monomer is characterized by an adiabatic electron affinity and electron vertical detachment energy of 0.72 and 1.08 eV (±0.05 eV), respectively. The electrophilicity results primarily from the bonding carbon-carbon interaction in the singly occupied molecular orbital of the anion, but it is further enhanced by intramolecular hydrogen bonds. The well-resolved structure in the photoelectron spectrum is reproduced theoretically, based on Franck-Condon factors for the vibronic anion → neutral transitions.

UR - http://www.scopus.com/inward/record.url?scp=84902477447&partnerID=8YFLogxK

U2 - 10.1063/1.4882655

DO - 10.1063/1.4882655

M3 - Article

C2 - 24929367

AN - SCOPUS:84902477447

SN - 0021-9606

VL - 140

JO - Journal of Chemical Physics

JF - Journal of Chemical Physics

IS - 22

M1 - 221103

ER -

Communication: Remarkable electrophilicity of the oxalic acid monomer: An anion photoelectron spectroscopy and theoretical study

Abstract

Access to Document

Other files and links

Fingerprint

Cite this