Intramolecular hydrogen bonding and molecular geometry of 4,6-dinitroresorcinol from gas-phase electron diffraction

Konstantin B. Borisenko, Károly Zauer, I. Hargittai

Research output: Contribution to journalArticle

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Abstract

The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (rg) and bond angles: (C-H)mean, 1.086 ± 0.015 Å; (C-C)mean, 1.402 ± 0.003 Å; C3-C4, 1.424 ± 0.005 Å; C-O, 1.341 ± 0.004 Å; O-H, 1.002 ± 0.009 Å; C-N, 1.461 ± 0.004 Å; (N-O)mean, 1.233 ± 0.003 Å; 〈C1-C2-C3, 120.3 ± 0.4°; 〈C2-C3-C4, 119.3 ± 0.3°; 〈C3-C4-C5, 121.6 ± 0.3°; 〈C4-C5-C6, 118.0 ± 0.4°; 〈C4-C3-O, 123.4 ± 0.3°; 〈C-O-H, 104.5 ± 1.4°; 〈C3-C4-N, 121.0 ± 0.2°; (〈C-N-O)mean, 118.1 ± 0.1°; 〈O-N-O, 123.7 ± 0.2°. The effective angle of nitro group torsion from electron diffraction is 14.4 ± 1.3°. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 ± 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.

Original languageEnglish
Pages (from-to)13808-13813
Number of pages6
JournalJournal of Physical Chemistry
Volume99
Issue number38
Publication statusPublished - 1995

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Nitrobenzene
Bond length
Electron diffraction
Torsional stress
Hydrogen bonds
electron diffraction
Gases
vapor phases
Geometry
nitrobenzenes
hydrogen
geometry
Phenol
Phenols
torsion
Conformations
Microwaves
torsional vibration
Molecules
phenols

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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Intramolecular hydrogen bonding and molecular geometry of 4,6-dinitroresorcinol from gas-phase electron diffraction. / Borisenko, Konstantin B.; Zauer, Károly; Hargittai, I.

In: Journal of Physical Chemistry, Vol. 99, No. 38, 1995, p. 13808-13813.

Research output: Contribution to journalArticle

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abstract = "The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (rg) and bond angles: (C-H)mean, 1.086 ± 0.015 {\AA}; (C-C)mean, 1.402 ± 0.003 {\AA}; C3-C4, 1.424 ± 0.005 {\AA}; C-O, 1.341 ± 0.004 {\AA}; O-H, 1.002 ± 0.009 {\AA}; C-N, 1.461 ± 0.004 {\AA}; (N-O)mean, 1.233 ± 0.003 {\AA}; 〈C1-C2-C3, 120.3 ± 0.4°; 〈C2-C3-C4, 119.3 ± 0.3°; 〈C3-C4-C5, 121.6 ± 0.3°; 〈C4-C5-C6, 118.0 ± 0.4°; 〈C4-C3-O, 123.4 ± 0.3°; 〈C-O-H, 104.5 ± 1.4°; 〈C3-C4-N, 121.0 ± 0.2°; (〈C-N-O)mean, 118.1 ± 0.1°; 〈O-N-O, 123.7 ± 0.2°. The effective angle of nitro group torsion from electron diffraction is 14.4 ± 1.3°. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 ± 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.",
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N2 - The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (rg) and bond angles: (C-H)mean, 1.086 ± 0.015 Å; (C-C)mean, 1.402 ± 0.003 Å; C3-C4, 1.424 ± 0.005 Å; C-O, 1.341 ± 0.004 Å; O-H, 1.002 ± 0.009 Å; C-N, 1.461 ± 0.004 Å; (N-O)mean, 1.233 ± 0.003 Å; 〈C1-C2-C3, 120.3 ± 0.4°; 〈C2-C3-C4, 119.3 ± 0.3°; 〈C3-C4-C5, 121.6 ± 0.3°; 〈C4-C5-C6, 118.0 ± 0.4°; 〈C4-C3-O, 123.4 ± 0.3°; 〈C-O-H, 104.5 ± 1.4°; 〈C3-C4-N, 121.0 ± 0.2°; (〈C-N-O)mean, 118.1 ± 0.1°; 〈O-N-O, 123.7 ± 0.2°. The effective angle of nitro group torsion from electron diffraction is 14.4 ± 1.3°. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 ± 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.

AB - The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (rg) and bond angles: (C-H)mean, 1.086 ± 0.015 Å; (C-C)mean, 1.402 ± 0.003 Å; C3-C4, 1.424 ± 0.005 Å; C-O, 1.341 ± 0.004 Å; O-H, 1.002 ± 0.009 Å; C-N, 1.461 ± 0.004 Å; (N-O)mean, 1.233 ± 0.003 Å; 〈C1-C2-C3, 120.3 ± 0.4°; 〈C2-C3-C4, 119.3 ± 0.3°; 〈C3-C4-C5, 121.6 ± 0.3°; 〈C4-C5-C6, 118.0 ± 0.4°; 〈C4-C3-O, 123.4 ± 0.3°; 〈C-O-H, 104.5 ± 1.4°; 〈C3-C4-N, 121.0 ± 0.2°; (〈C-N-O)mean, 118.1 ± 0.1°; 〈O-N-O, 123.7 ± 0.2°. The effective angle of nitro group torsion from electron diffraction is 14.4 ± 1.3°. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 ± 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.

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