Molecular and electronic structure of zwitterionic diamino-meta-quinonoid molecules

Hung Thanh Le, Pham Cam Nam, Van Luong Dao, T. Veszprémi, Minh Tho Nguyen

Research output: Contribution to journalArticle

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Abstract

Quantum chemical calculations using molecular orbital (HF, CASSCF) and density functional theory (B3LYP) methods, in conjunction with the 6-311 + + G(d,p) basis set, have been applied to investigate the molecular and electronic structure of two diamino-meta-quinonoid molecules 1a and 2a, each containing a six-membered ring coupled with two exocyclic C = O bonds situated in a meta position, along with two amino substituents (NH2 and NH-CH3). It is confirmed that these substituted meta-quinone systems exhibit a zwitterionic structure in which the positively charged N-C-C(H)-C-N subunit, containing the two amino-groups, forms two chemical bonds with the negatively charged O-C-C(H)-C-O subunit. The negative charge amounts to about half of an electron. The charge separation has been approached in terms of geometries, vibrational frequencies, and electronic distribution. The ionization energy for molecule 1a is about 7.8 ± 0.3 eV. The quinonoid systems are essentially non-aromatic characterized by the NICS(+1) values of around 1.2 ppm.

Original languageEnglish
Pages (from-to)2347-2355
Number of pages9
JournalMolecular Physics
Volume101
Issue number15
Publication statusPublished - Aug 10 2003

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Molecular Structure
Molecular structure
Electronic structure
molecular structure
Electrons
electronic structure
Molecules
Ionization potential
Chemical bonds
quinones
Vibrational spectra
Molecular orbitals
polarization (charge separation)
chemical bonds
Density functional theory
molecules
molecular orbitals
density functional theory
ionization
Geometry

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics

Cite this

Le, H. T., Nam, P. C., Dao, V. L., Veszprémi, T., & Nguyen, M. T. (2003). Molecular and electronic structure of zwitterionic diamino-meta-quinonoid molecules. Molecular Physics, 101(15), 2347-2355.

Molecular and electronic structure of zwitterionic diamino-meta-quinonoid molecules. / Le, Hung Thanh; Nam, Pham Cam; Dao, Van Luong; Veszprémi, T.; Nguyen, Minh Tho.

In: Molecular Physics, Vol. 101, No. 15, 10.08.2003, p. 2347-2355.

Research output: Contribution to journalArticle

Le, HT, Nam, PC, Dao, VL, Veszprémi, T & Nguyen, MT 2003, 'Molecular and electronic structure of zwitterionic diamino-meta-quinonoid molecules', Molecular Physics, vol. 101, no. 15, pp. 2347-2355.
Le, Hung Thanh ; Nam, Pham Cam ; Dao, Van Luong ; Veszprémi, T. ; Nguyen, Minh Tho. / Molecular and electronic structure of zwitterionic diamino-meta-quinonoid molecules. In: Molecular Physics. 2003 ; Vol. 101, No. 15. pp. 2347-2355.
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AU - Nguyen, Minh Tho

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N2 - Quantum chemical calculations using molecular orbital (HF, CASSCF) and density functional theory (B3LYP) methods, in conjunction with the 6-311 + + G(d,p) basis set, have been applied to investigate the molecular and electronic structure of two diamino-meta-quinonoid molecules 1a and 2a, each containing a six-membered ring coupled with two exocyclic C = O bonds situated in a meta position, along with two amino substituents (NH2 and NH-CH3). It is confirmed that these substituted meta-quinone systems exhibit a zwitterionic structure in which the positively charged N-C-C(H)-C-N subunit, containing the two amino-groups, forms two chemical bonds with the negatively charged O-C-C(H)-C-O subunit. The negative charge amounts to about half of an electron. The charge separation has been approached in terms of geometries, vibrational frequencies, and electronic distribution. The ionization energy for molecule 1a is about 7.8 ± 0.3 eV. The quinonoid systems are essentially non-aromatic characterized by the NICS(+1) values of around 1.2 ppm.

AB - Quantum chemical calculations using molecular orbital (HF, CASSCF) and density functional theory (B3LYP) methods, in conjunction with the 6-311 + + G(d,p) basis set, have been applied to investigate the molecular and electronic structure of two diamino-meta-quinonoid molecules 1a and 2a, each containing a six-membered ring coupled with two exocyclic C = O bonds situated in a meta position, along with two amino substituents (NH2 and NH-CH3). It is confirmed that these substituted meta-quinone systems exhibit a zwitterionic structure in which the positively charged N-C-C(H)-C-N subunit, containing the two amino-groups, forms two chemical bonds with the negatively charged O-C-C(H)-C-O subunit. The negative charge amounts to about half of an electron. The charge separation has been approached in terms of geometries, vibrational frequencies, and electronic distribution. The ionization energy for molecule 1a is about 7.8 ± 0.3 eV. The quinonoid systems are essentially non-aromatic characterized by the NICS(+1) values of around 1.2 ppm.

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