Synthesis, characterization and crystal structure of (2Z)-3-[(4- methylphenyl)amino]-1-phenylbut-2-en-1-one

Siddappa A. Patil; Diego Gonzalez-Flores; Phillip A. Medina; Jason K. Vohs; Seth Dever; Joshua Popp; Michael Stentzel; Leslie W. Pineda; Mavis L. Montero; Bradley D. Fahlman

doi:10.1007/s10870-012-0279-8

Synthesis, characterization and crystal structure of (2Z)-3-[(4- methylphenyl)amino]-1-phenylbut-2-en-1-one

Siddappa A. Patil, Diego Gonzalez-Flores, Phillip A. Medina, Jason K. Vohs, Seth Dever, Joshua Popp, Michael Stentzel, Leslie W. Pineda, Mavis L. Montero, Bradley D. Fahlman

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Abstract

The compound (2Z)-3-[(4-methylphenyl)amino]- 1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by ¹ H NMR, ¹³ C NMR, IR, mass spectrometry, elemental analysis, TGA/DSC and single crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pccn (No. 56) with a = 17.0042(18) Å, b = 11.5826(13) Å, c = 14.0514(15) Å, V = 2767.5(5) Å ³ and Z = 8. Data collection on 223(2) K resulted its structure with R1 = 0.0449, wR2 = 0.0980. The molecules in the unit cell are arranged in layers. The intramolecular hydrogen bonds of the type N-H· · ·O were observed in the structure. The compound exhibits two distinct endothermic peaks at a temperature 94.70 °C and 232.60 °C corresponding to melting and boiling points respectively.

Original language	English
Pages (from-to)	560-565
Number of pages	6
Journal	Journal of Chemical Crystallography
Volume	42
Issue number	6
DOIs	https://doi.org/10.1007/s10870-012-0279-8
State	Published - Jun 2012

Keywords

(2Z)-3-[(4-Methylphenyl)amino]-1- phenylbut-2-en-1-one
Crystal structure
Spectroscopy
Synthesis
Thermogravimetric Analysis

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10.1007/s10870-012-0279-8

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@article{46becc226eb34d899cdf24767bf5bcd9,

title = "Synthesis, characterization and crystal structure of (2Z)-3-[(4- methylphenyl)amino]-1-phenylbut-2-en-1-one",

abstract = " The compound (2Z)-3-[(4-methylphenyl)amino]- 1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by 1 H NMR, 13 C NMR, IR, mass spectrometry, elemental analysis, TGA/DSC and single crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pccn (No. 56) with a = 17.0042(18) {\AA}, b = 11.5826(13) {\AA}, c = 14.0514(15) {\AA}, V = 2767.5(5) {\AA} 3 and Z = 8. Data collection on 223(2) K resulted its structure with R1 = 0.0449, wR2 = 0.0980. The molecules in the unit cell are arranged in layers. The intramolecular hydrogen bonds of the type N-H· · ·O were observed in the structure. The compound exhibits two distinct endothermic peaks at a temperature 94.70 °C and 232.60 °C corresponding to melting and boiling points respectively.",

keywords = "(2Z)-3-[(4-Methylphenyl)amino]-1- phenylbut-2-en-1-one, Crystal structure, Spectroscopy, Synthesis, Thermogravimetric Analysis",

author = "Patil, {Siddappa A.} and Diego Gonzalez-Flores and Medina, {Phillip A.} and Vohs, {Jason K.} and Seth Dever and Joshua Popp and Michael Stentzel and Pineda, {Leslie W.} and Montero, {Mavis L.} and Fahlman, {Bradley D.}",

note = "Funding Information: Acknowledgments The authors would like to thank the National Science Foundation (CHE-0911061) for financial support. We also acknowledge the Ministerio de Ciencia y Tecnolog{\'i}a de Costa Rica (MICIT), Consejo Nacional para Investigaciones Cient{\'i}ficas y Tec-nol{\'o}gicas (CONICIT), and the Centro de Electroqu{\'i}mica y Energ{\'i}a Qu{\'i}mica (CELEQ) at the Universidad de Costa Rica for providing partial financial support for an internship for Diego Gonzalez-Flores at Central Michigan University.",

year = "2012",

month = jun,

doi = "10.1007/s10870-012-0279-8",

language = "English",

volume = "42",

pages = "560--565",

journal = "Journal of Chemical Crystallography",

issn = "1074-1542",

publisher = "Journal of Chemical Crystallography",

number = "6",

}

TY - JOUR

T1 - Synthesis, characterization and crystal structure of (2Z)-3-[(4- methylphenyl)amino]-1-phenylbut-2-en-1-one

AU - Patil, Siddappa A.

AU - Gonzalez-Flores, Diego

AU - Medina, Phillip A.

AU - Vohs, Jason K.

AU - Dever, Seth

AU - Popp, Joshua

AU - Stentzel, Michael

AU - Pineda, Leslie W.

AU - Montero, Mavis L.

AU - Fahlman, Bradley D.

N1 - Funding Information: Acknowledgments The authors would like to thank the National Science Foundation (CHE-0911061) for financial support. We also acknowledge the Ministerio de Ciencia y Tecnología de Costa Rica (MICIT), Consejo Nacional para Investigaciones Científicas y Tec-nológicas (CONICIT), and the Centro de Electroquímica y Energía Química (CELEQ) at the Universidad de Costa Rica for providing partial financial support for an internship for Diego Gonzalez-Flores at Central Michigan University.

PY - 2012/6

Y1 - 2012/6

N2 - The compound (2Z)-3-[(4-methylphenyl)amino]- 1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by 1 H NMR, 13 C NMR, IR, mass spectrometry, elemental analysis, TGA/DSC and single crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pccn (No. 56) with a = 17.0042(18) Å, b = 11.5826(13) Å, c = 14.0514(15) Å, V = 2767.5(5) Å 3 and Z = 8. Data collection on 223(2) K resulted its structure with R1 = 0.0449, wR2 = 0.0980. The molecules in the unit cell are arranged in layers. The intramolecular hydrogen bonds of the type N-H· · ·O were observed in the structure. The compound exhibits two distinct endothermic peaks at a temperature 94.70 °C and 232.60 °C corresponding to melting and boiling points respectively.

AB - The compound (2Z)-3-[(4-methylphenyl)amino]- 1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by 1 H NMR, 13 C NMR, IR, mass spectrometry, elemental analysis, TGA/DSC and single crystal X-ray diffraction. The title compound crystallizes in the orthorhombic space group Pccn (No. 56) with a = 17.0042(18) Å, b = 11.5826(13) Å, c = 14.0514(15) Å, V = 2767.5(5) Å 3 and Z = 8. Data collection on 223(2) K resulted its structure with R1 = 0.0449, wR2 = 0.0980. The molecules in the unit cell are arranged in layers. The intramolecular hydrogen bonds of the type N-H· · ·O were observed in the structure. The compound exhibits two distinct endothermic peaks at a temperature 94.70 °C and 232.60 °C corresponding to melting and boiling points respectively.

KW - (2Z)-3-[(4-Methylphenyl)amino]-1- phenylbut-2-en-1-one

KW - Crystal structure

KW - Spectroscopy

KW - Synthesis

KW - Thermogravimetric Analysis

UR - http://www.scopus.com/inward/record.url?scp=84864644833&partnerID=8YFLogxK

U2 - 10.1007/s10870-012-0279-8

DO - 10.1007/s10870-012-0279-8

M3 - Article

AN - SCOPUS:84864644833

VL - 42

SP - 560

EP - 565

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

SN - 1074-1542

IS - 6

ER -

Synthesis, characterization and crystal structure of (2Z)-3-[(4- methylphenyl)amino]-1-phenylbut-2-en-1-one

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Keywords

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