SPONTANEOUS alpha-METHYLATION OF AN alpha-BROMOKETONE FROM DMF: SYNTHESIS AND CRYSTALLINE STRUCTURE OF 1,1 '-(3,4-DIPHENYLTHIENO[2,3-b]THIOPHENE-2,5-DIYL)BIS (PROPAN-1-ONE)

In this work, we have obtained 1,1'-(3,4-diphenylthieno-[2,3-b]thiophene-2,5-diyl-)bis(propan-l-one) (3), via recrystallization of 1,1'-(3, 4-diphenylthieno[2,3-b]thiophene-2,5-diyl)bis(2-bromoethanone) (2) from a mixture of DMF and chloroform. Structure of compound 3 was confirmed by sing...

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Published inHeterocycles Vol. 94; no. 4; pp. 657 - 665
Main Authors Mabkhot, Yahia N., Al-Showiman, Salim S., Soliman, Saied. M., Ghabbour, Hazem A., Ben Hadda, Taibi, Warad, Ismail, Boshaala, Ahmed
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
X -Ray Diffraction
NMR Spectrum
POTENT
DFT
1,1 '-(3,4-Diphenylthieno[2,3-b]thiophene-2,5-diyl)bis(propan-1-one)
ANALOGS
Thiophene
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Summary:In this work, we have obtained 1,1'-(3,4-diphenylthieno-[2,3-b]thiophene-2,5-diyl-)bis(propan-l-one) (3), via recrystallization of 1,1'-(3, 4-diphenylthieno[2,3-b]thiophene-2,5-diyl)bis(2-bromoethanone) (2) from a mixture of DMF and chloroform. Structure of compound 3 was confirmed by single X-ray diffraction. The compound crystallizes in the orthorhombic, Pbcn with a =13.6934 (5) (A) over circle, b =19.3166 (6) (A) over circle, c =7.4283 (3) (A) over circle, V = 1964.86 (12) ((A) over circle (3)), and Z = 4. Optimized molecular structure calculations with the aid of B3LYP/6-31G (d, p) DFT agreed well with experimental results obtained from X-ray data. Calculations revealed that the two bivalent sulfur atoms have electropositive nature whereas the two O-atoms are electronegative.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-16-13605