Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation

Laura C. Cabrera-Pérez; Efrén V. Garciá-Baéz; Marina O. Franco-Hernández; Francisco J. Martínez-Martínez; Itzia I. Padilla-Martínez

doi:10.1107/S2053229615006725

Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation

Laura C. Cabrera-Pérez, Efrén V. Garciá-Baéz, Marina O. Franco-Hernández, Francisco J. Martínez-Martínez, Itzia I. Padilla-Martínez

Unidad Profesional Interdisciplinaria de Biotecnología (UPIBI)

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Abstract

The title compound, C₁₂H₁₃NO₄, is one of the few examples that exhibits a syn conformation between the amide and ester carbonyl groups of the oxalyl group. This conformation allows the engagement of the amide H atom in an intramolecular three-centred hydrogen-bonding S(6)S(5) motif. The compound is self-assembled by C=O⋯C=O and amide-π interactions into stacked columns along the b-axis direction. The concurrence of both interactions seems to be responsible for stabilizing the observed syn conformation between the carbonyl groups. The second dimension, along the a-axis direction, is developed by soft C-H⋯O hydrogen bonding. Density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) level of theory were performed to support the experimental findings.

Original language	English
Pages (from-to)	381-385
Number of pages	5
Journal	Acta Crystallographica Section C: Structural Chemistry
Volume	71
DOIs	https://doi.org/10.1107/S2053229615006725
State	Published - 1 May 2015

Keywords

amide-π interaction
bond energy profile
carbonyl-carbonyl interaction
computational chemistry
crystal structure
molecular clefts
oxamate
three-centre hydrogen bond

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Cabrera-Pérez, L. C., Garciá-Baéz, E. V., Franco-Hernández, M. O., Martínez-Martínez, F. J., & Padilla-Martínez, I. I. (2015). Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation. Acta Crystallographica Section C: Structural Chemistry, 71, 381-385. https://doi.org/10.1107/S2053229615006725

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title = "Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation",

abstract = "The title compound, C12H13NO4, is one of the few examples that exhibits a syn conformation between the amide and ester carbonyl groups of the oxalyl group. This conformation allows the engagement of the amide H atom in an intramolecular three-centred hydrogen-bonding S(6)S(5) motif. The compound is self-assembled by C=O⋯C=O and amide-π interactions into stacked columns along the b-axis direction. The concurrence of both interactions seems to be responsible for stabilizing the observed syn conformation between the carbonyl groups. The second dimension, along the a-axis direction, is developed by soft C-H⋯O hydrogen bonding. Density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) level of theory were performed to support the experimental findings.",

keywords = "amide-π interaction, bond energy profile, carbonyl-carbonyl interaction, computational chemistry, crystal structure, molecular clefts, oxamate, three-centre hydrogen bond",

author = "Cabrera-P{\'e}rez, {Laura C.} and Garci{\'a}-Ba{\'e}z, {Efr{\'e}n V.} and Franco-Hern{\'a}ndez, {Marina O.} and Mart{\'i}nez-Mart{\'i}nez, {Francisco J.} and Padilla-Mart{\'i}nez, {Itzia I.}",

note = "Publisher Copyright: {\textcopyright} 2015 International Union of Crystallography.",

year = "2015",

month = may,

day = "1",

doi = "10.1107/S2053229615006725",

language = "Ingl{\'e}s",

volume = "71",

pages = "381--385",

journal = "Acta Crystallographica Section C: Structural Chemistry",

issn = "2053-2296",

}

Cabrera-Pérez, LC , Garciá-Baéz, EV , Franco-Hernández, MO, Martínez-Martínez, FJ & Padilla-Martínez, II 2015, 'Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation', Acta Crystallographica Section C: Structural Chemistry, vol. 71, pp. 381-385. https://doi.org/10.1107/S2053229615006725

Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation. / Cabrera-Pérez, Laura C.; Garciá-Baéz, Efrén V.; Franco-Hernández, Marina O. et al.
In: Acta Crystallographica Section C: Structural Chemistry, Vol. 71, 01.05.2015, p. 381-385.

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

TY - JOUR

T1 - Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation

AU - Cabrera-Pérez, Laura C.

AU - Garciá-Baéz, Efrén V.

AU - Franco-Hernández, Marina O.

AU - Martínez-Martínez, Francisco J.

AU - Padilla-Martínez, Itzia I.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - The title compound, C12H13NO4, is one of the few examples that exhibits a syn conformation between the amide and ester carbonyl groups of the oxalyl group. This conformation allows the engagement of the amide H atom in an intramolecular three-centred hydrogen-bonding S(6)S(5) motif. The compound is self-assembled by C=O⋯C=O and amide-π interactions into stacked columns along the b-axis direction. The concurrence of both interactions seems to be responsible for stabilizing the observed syn conformation between the carbonyl groups. The second dimension, along the a-axis direction, is developed by soft C-H⋯O hydrogen bonding. Density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) level of theory were performed to support the experimental findings.

AB - The title compound, C12H13NO4, is one of the few examples that exhibits a syn conformation between the amide and ester carbonyl groups of the oxalyl group. This conformation allows the engagement of the amide H atom in an intramolecular three-centred hydrogen-bonding S(6)S(5) motif. The compound is self-assembled by C=O⋯C=O and amide-π interactions into stacked columns along the b-axis direction. The concurrence of both interactions seems to be responsible for stabilizing the observed syn conformation between the carbonyl groups. The second dimension, along the a-axis direction, is developed by soft C-H⋯O hydrogen bonding. Density functional theory (DFT) calculations at the B3LYP/6-31G(d,p) level of theory were performed to support the experimental findings.

KW - amide-π interaction

KW - bond energy profile

KW - carbonyl-carbonyl interaction

KW - computational chemistry

KW - crystal structure

KW - molecular clefts

KW - oxamate

KW - three-centre hydrogen bond

UR - http://www.scopus.com/inward/record.url?scp=84928882654&partnerID=8YFLogxK

U2 - 10.1107/S2053229615006725

DO - 10.1107/S2053229615006725

M3 - Artículo

C2 - 25940894

SN - 2053-2296

VL - 71

SP - 381

EP - 385

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

ER -

Cabrera-Pérez LC , Garciá-Baéz EV , Franco-Hernández MO, Martínez-Martínez FJ, Padilla-Martínez II. Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation. Acta Crystallographica Section C: Structural Chemistry. 2015 May 1;71:381-385. doi: 10.1107/S2053229615006725

Carbonyl-carbonyl interactions and amide π-stacking as the directing motifs of the supramolecular assembly of ethyl N-(2-acetylphenyl)oxalamate in a synperiplanar conformation

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Keywords

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