Magnetic non-equivalence of protons in a sulfinyl carbanion

H. Kloosterziel

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

The 100 MHz. 1H N.M.R. spectra of Ph2C-R (I) were recorded in liq. NH3 at various temps. For I (R = H) the 2 para protons appeared as 1 triplet at temps. -20 to -60 Deg; the ortho protons appeared as 1 singlet at -20 Deg, but as 2 doublets at -60 Deg as a result of hindered rotation about the C-1-C (aryl) bonds. Spectra of I (R = MeS or MeSO2) were temp. independent and indicate free rotation about these bonds, -20 to -60 Deg. At -20 Deg, protons of I (R = MeSO) gave rise to a 4:4:2 pattern. With decreasing temp., these signals broadened, then sharpened again. At -73 Deg, the para protons gave rise to 2 triplets (coupling const. J = 7.2 Hz.) of triplets (J = 1.2 Hz.) with chem. shifts 6.34 and 6.62 ppm. The nonequivalence of the para protons at the lower temps. indicates that the two rings have different amts. of neg. charge which may be caused by different electrostatic interactions or by different torsions about the C-1-C (aryl) bonds. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)1330-1331
Number of pages2
JournalChemical Communications
Volume21
DOIs
Publication statusPublished - 1968

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