Synthesis, characterization, spectroscopic and X-ray diffraction studies of novel pair of thiourea derivatives of 2-morpholin-4-yl-ethylamine

Ibrahim N. Hassan, Faszly Rahm, Sharina Abu Hanifah, Mou'ad A. Tarawneh, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A novel pair of thiourea derivatives of cinnamoyl and benzoyl with 2-morpholin-4-yl-ethylamine namely 1-(2-morpholinoethyl)-3-cinnamoylthiourea (I) and 1-(2-morpholinoethyl)-3-benzoylthiourea (II) have been successfully synthesized and characterized via IR, NMR, CHNS-O, UV techniques and X-ray diffraction for single crystal. The important stretching bands for v(C=O), v(N-H), v(C=S) and v(C-N) were around 1600, 3300, 700 and 1300 cm-1, respectively, were shown by IR spectra. There is an important chromophore, C=O, observed in the UV spectra with a maximum absorption at around 240 nm. The crystal structures of (I) and (II) have been determined by X-ray diffraction analysis for single crystal. Both the molecules adopt trans-cis configuration relative to the position of phenyl ring and 2-morpholin-4-yl-ethyl groups with respect to the thiono S atom, across C-N bonds. In both compounds, there were two intramolecular hydrogen bonds, N-H···O and N-H···N, that form of pseudo-six-membered and pseudo-five-membered rings, respectively, in addition to a pseudo-five-membered ring, C7-H6···O1, in (I) which stabilizes the molecule. In the crystal frame, the molecules were linked by intermolecular hydrogen bonds N-H···O and C-H···O forming polymeric (I) and chain network (II). 1H NMR spectra show chemical shift at δh 10.86-10.97 ppm and δH 9.07-9.12 ppm were assigned for NH protons. While the chemical shift for 13C NMR analysis of C=S and C=O presence at δC 169-179 ppm.

Original languageEnglish
Pages (from-to)3711-3715
Number of pages5
JournalAsian Journal of Chemistry
Volume27
Issue number10
DOIs
Publication statusPublished - 1 Oct 2015

Fingerprint

Thiourea
Nuclear magnetic resonance
Chemical shift
Derivatives
X ray diffraction
Molecules
Hydrogen bonds
Single crystals
Chromophores
X ray diffraction analysis
Stretching
Protons
Crystal structure
Atoms
Crystals
ethylamine

Keywords

  • 2-morpholin-4-yl-ethylamine
  • Benzoyl
  • Thiourea
  • X-ray crystallography

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis, characterization, spectroscopic and X-ray diffraction studies of novel pair of thiourea derivatives of 2-morpholin-4-yl-ethylamine. / Hassan, Ibrahim N.; Rahm, Faszly; Abu Hanifah, Sharina; Tarawneh, Mou'ad A.; Mohd. Yamin, Bohari.

In: Asian Journal of Chemistry, Vol. 27, No. 10, 01.10.2015, p. 3711-3715.

Research output: Contribution to journalArticle

Hassan, Ibrahim N. ; Rahm, Faszly ; Abu Hanifah, Sharina ; Tarawneh, Mou'ad A. ; Mohd. Yamin, Bohari. / Synthesis, characterization, spectroscopic and X-ray diffraction studies of novel pair of thiourea derivatives of 2-morpholin-4-yl-ethylamine. In: Asian Journal of Chemistry. 2015 ; Vol. 27, No. 10. pp. 3711-3715.
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T1 - Synthesis, characterization, spectroscopic and X-ray diffraction studies of novel pair of thiourea derivatives of 2-morpholin-4-yl-ethylamine

AU - Hassan, Ibrahim N.

AU - Rahm, Faszly

AU - Abu Hanifah, Sharina

AU - Tarawneh, Mou'ad A.

AU - Mohd. Yamin, Bohari

PY - 2015/10/1

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N2 - A novel pair of thiourea derivatives of cinnamoyl and benzoyl with 2-morpholin-4-yl-ethylamine namely 1-(2-morpholinoethyl)-3-cinnamoylthiourea (I) and 1-(2-morpholinoethyl)-3-benzoylthiourea (II) have been successfully synthesized and characterized via IR, NMR, CHNS-O, UV techniques and X-ray diffraction for single crystal. The important stretching bands for v(C=O), v(N-H), v(C=S) and v(C-N) were around 1600, 3300, 700 and 1300 cm-1, respectively, were shown by IR spectra. There is an important chromophore, C=O, observed in the UV spectra with a maximum absorption at around 240 nm. The crystal structures of (I) and (II) have been determined by X-ray diffraction analysis for single crystal. Both the molecules adopt trans-cis configuration relative to the position of phenyl ring and 2-morpholin-4-yl-ethyl groups with respect to the thiono S atom, across C-N bonds. In both compounds, there were two intramolecular hydrogen bonds, N-H···O and N-H···N, that form of pseudo-six-membered and pseudo-five-membered rings, respectively, in addition to a pseudo-five-membered ring, C7-H6···O1, in (I) which stabilizes the molecule. In the crystal frame, the molecules were linked by intermolecular hydrogen bonds N-H···O and C-H···O forming polymeric (I) and chain network (II). 1H NMR spectra show chemical shift at δh 10.86-10.97 ppm and δH 9.07-9.12 ppm were assigned for NH protons. While the chemical shift for 13C NMR analysis of C=S and C=O presence at δC 169-179 ppm.

AB - A novel pair of thiourea derivatives of cinnamoyl and benzoyl with 2-morpholin-4-yl-ethylamine namely 1-(2-morpholinoethyl)-3-cinnamoylthiourea (I) and 1-(2-morpholinoethyl)-3-benzoylthiourea (II) have been successfully synthesized and characterized via IR, NMR, CHNS-O, UV techniques and X-ray diffraction for single crystal. The important stretching bands for v(C=O), v(N-H), v(C=S) and v(C-N) were around 1600, 3300, 700 and 1300 cm-1, respectively, were shown by IR spectra. There is an important chromophore, C=O, observed in the UV spectra with a maximum absorption at around 240 nm. The crystal structures of (I) and (II) have been determined by X-ray diffraction analysis for single crystal. Both the molecules adopt trans-cis configuration relative to the position of phenyl ring and 2-morpholin-4-yl-ethyl groups with respect to the thiono S atom, across C-N bonds. In both compounds, there were two intramolecular hydrogen bonds, N-H···O and N-H···N, that form of pseudo-six-membered and pseudo-five-membered rings, respectively, in addition to a pseudo-five-membered ring, C7-H6···O1, in (I) which stabilizes the molecule. In the crystal frame, the molecules were linked by intermolecular hydrogen bonds N-H···O and C-H···O forming polymeric (I) and chain network (II). 1H NMR spectra show chemical shift at δh 10.86-10.97 ppm and δH 9.07-9.12 ppm were assigned for NH protons. While the chemical shift for 13C NMR analysis of C=S and C=O presence at δC 169-179 ppm.

KW - 2-morpholin-4-yl-ethylamine

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KW - Thiourea

KW - X-ray crystallography

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