title: Isolation of 3-amino-4-nitro-benzyl acetate: evidence of an undisclosed impurity in 5-amino-2-nitro-benzoic acid.
abstract: Yellow crystals of the title compound 3-amino-4-nitro-benzyl acetate, C9H10N2O4, were isolated from the reaction of acetic anhydride with (5-amino-2-nitro-phen-yl)methanol, prepared from reduction of commerically available 5-amino-2-nitro-benzoic acid with borane-THF. The mol-ecule is essentially planar (r.m.s. deviation = 0.028 Å). The mol-ecules are linked by inter-molecular N-H⋯O hydrogen-bonding inter-actions between the carbonyl and amine groups, forming a zigzag chain along the b-axis direction lying in a plane parallel to (-102). The chains are stacked along the c axis by π-π inter-actions [centroid-centroid distances = 3.6240 (3) and 3.5855 (4) Å]. A strong intra-molecular N-H⋯O hydrogen-bonding inter-action is observed between the nitro group and the amine group [2.660 (2) Å].
authors.affiliation: Department of Chemistry and Physics, Armstrong State University, 11935 Abercorn Street, Savannah GA 31419, USA.
authors.forename: Brandon
authors.initials: B
authors.lastname: Quillian
authors.affiliation: Department of Chemistry and Physics, Armstrong State University, 11935 Abercorn Street, Savannah GA 31419, USA.
authors.forename: Jordan
authors.initials: J
authors.lastname: Hendricks
authors.affiliation: Department of Chemistry and Physics, Armstrong State University, 11935 Abercorn Street, Savannah GA 31419, USA.
authors.forename: Matthew
authors.initials: M
authors.lastname: Trivitayakhun
authors.affiliation: Department of Chemistry and Physics, Armstrong State University, 11935 Abercorn Street, Savannah GA 31419, USA.
authors.forename: Clifford W
authors.initials: CW
authors.lastname: Padgett
keywords: 3-amino-4-nitro­benzyl acetate; 5-amino-2-nitro­benzoic acid; crystal structure; inter­molecular; intra­molecular; resonance-assisted hydrogen bonding