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( E )-2-[(2-Hydroxy-5-nitrophenyl)iminiomethyl]phenolate

Journal Article · · Acta Crystallographica. Section E
 [1];  [2];  [3];  [4]
  1. Morgan State Univ., Baltimore, MD (United States). Dept. of Chemistry; DOE/OSTI
  2. Morgan State Univ., Baltimore, MD (United States). Dept. of Chemistry
  3. Howard Univ., Washington, DC (United States). Dept. of Chemistry
  4. Keene State College, Keene, NH (United States). Dept. of Chemistry
+ Show Author Affiliations
In the title molecule, C13H10N2O4, the dihedral angle between the mean planes of the benzene and phenolate rings is 21.6 (4)°. The nitro O atoms are twisted slightly out of the plane of the ring to which the nitro group is attached [dihedral angle 8.4 (3)°]. The amine group forms an intramolecular hydrogen bond with both nearby O atoms. An extended delocalization throughout the entire molecule exists producing a zwitterionic effect in this region of the molecule. The shortened C—O bond [1.2997 (15) Å ] in concert with the slightly longer C—OH bond [1.3310 (16) Å ] provide evidence for this effect. The crystal packing is influenced by strong intermolecular O—HO hydrogen bonding. As a result, molecules are linked into an infinite zigzag chain running along the b axis. A MOPAC PM3 calculation provides support to these observations.
Research Organization:
Morgan State Univ., Baltimore, MD (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
Grant/Contract Number:
FG02-03ER63580
OSTI ID:
1625729
Journal Information:
Acta Crystallographica. Section E, Journal Name: Acta Crystallographica. Section E Journal Issue: 3 Vol. 65; ISSN 1600-5368; ISSN ACSEBH
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
English

References (10)

Imino Diels–Alder reaction of boronates: A new route to 3,4-dihydroquinolines journal June 2005
Synthesis and photophysical characterization of a Schiff base as anion sensor journal March 2009
2-[(2-Hydroxy-4-nitrophenyl)aminomethylene]cyclohexa-3,5-dien-1(2 H )-one journal September 2003
N-(2-Hydroxyphenyl)salicylaldimine journal November 1995
A short history of SHELX journal December 2007
( Z )-6-[(2-Methoxyphenylamino)methylene]-4-methylcyclohexa-2,4-dien-1(2 H )-one monohydrate journal February 2006
(6 Z )-3-Diethylamino-6-(3-hydroxyanilinomethylene)cyclohexa-2,4-dien-1-one journal November 2007
( E )-2-[(2-Hydroxy-5-nitrophenyl)iminiomethyl]-4-nitrophenolate journal January 2009
Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles journal January 2001
Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles journal August 2001

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Crystallography