Proton magnetic resonance spectra of tetravinyltin and tetraallyltin: dx-px bonding

Blears, D. J.; Danyluk, S.; Cawley, S.

doi:10.1016/s0022-328x(00)88740-9

Cited by 25 publications

(4 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The positions of the v(C=C) bands in the solid state spectra of the two 2,2'-bipyridyl derivatives (which dissociate in solution) are close to those of the corresponding bands recorded for dimethylsulfoxide solutions of the parent compounds. It was of interest to include divinyltin dichloride in these studies where, although n-interactions of the type shown in 1 are not possible, dn-pn character in the Sn-C bonds may be present (12). The i.r.…”

Section: Resultsmentioning

confidence: 99%

π-Bonding between C=C bonds and tin in alkenyltin compounds

Clark¹,

Poller²

1970

Can. J. Chem.

View full text Add to dashboard Cite

The infrared and nuclear magnetic resonance spectra of a number of allyl-, but-3-enyl-, crotyl-, and vinyl-tin compounds in dimethylsulfoxide have been examined and compared with measurements made on solutions in methylene chloride and carbon tetrachloride. It is concluded from the changes which occur in the positions of the v(C=C) bands and in the chemical shifts of the olefinic protons that there are no significant n-interactions between the d orbitals on tin and the olefinic n-systems.

show abstract

Section: Resultsmentioning

confidence: 99%

π-Bonding between C=C bonds and tin in alkenyltin compounds

Clark¹,

Poller²

1970

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…Upon reduction with sodium hydrosulfite the starting material was retrieved: ir 1651 (C=0), 1600 (C=C), 3340, 1300, 1050 (CH2OH) cm"1; nmr r 3.23 (m), 6.15 (t), 7.31 (m), and 7.93 ppm (d). 18 1,4-Dimethoxy-2-(2 ',2 '-dicarbethoxyethyl)benzene (IV).-This substance was prepared from 1,4-dimethoxy-3-chloromethylbenzene by a standard malonic ester synthesis as a colorless liquid, bp 157-160°(0.5 mm); yield, 70%; nmr 3.38 (s), 5.92 (qu), 6.26 (s), 6.32 (t), 6.33 (s), 6.42 (d), 8.84 (t). 18 1,4-Dihydroxy-2 (3 '-propanoic acid)benzene (V).-Compound IV was refluxed for 4 hr with 48% hydrogen bromide.…”

Section: Methodsmentioning

confidence: 99%

Electron-transfer polymers. XXXV. Inductive effects of substituents upon spectral and redox properties of p-benzoquinones

Wegner¹,

Keyes²,

Nakabayashi³

et al. 1969

J. Org. Chem.

View full text Add to dashboard Cite

“…A number of attempts have been made recently to rationalize the deshieldings of vinyl protons in ally1 and aryl silanes, germanes, and stannanes in terms of a resonance interaction between d, orbitals of the M atom and the p, orbitals of the vinyl group (7,8,20,(26)(27)(28). The deshieldings, i.e.…”

Section: Comparison With Earlier Parametersmentioning

confidence: 99%

Proton magnetic resonance spectra of vinylmetallic compounds. Part I. Tetravinyl and triphenylvinyl derivatives of Group IVB elements

Cawley¹,

Danyluk²

1968

Can. J. Chem.

View full text Add to dashboard Cite

A study has been made of the proton magnetic resonance spectra for all of the Group IVB derivatives of the series MVi, and 43MVi (4 = phenyl group and Vi = vinyl group). The spectra were measured at 60 MHz as accurately as possible and the assignment of transitions was checked with a variety of supplemental aids including double irradiation, nlultiple quantum transitions, and medium effects. Final, accurate spectral parameters were derived using both iterative and exact comp~~tational methods for solution of the three-spin problem. Excellent agreement was obtained between the sets of parameters determined by the two methods.The clien~ical shifts for both series of compounds display a nunlber of characteristic trends of which the most notable is a displacenlent of the vinyl proton signals to low field with increasing atomic number of the M atom. In each series the largest shift change is noted in going from the carbon to the silicon dcrivative. These deshicldings have been attributed to the enhanced possibility of d,-p, interaction between the central M atoll1 and the vinyl group in higher nlenlbers of the series. Marked changes are also noted for the internal shifts of the vinyl protons down both series of compounds. It is concluded that these changes are principally due to the effects of the M-C bond diamagnetic anisotropy. The trends in internal shifts can be satisfactorily reproduced by the dipole approxin~ation using AX values of 4, 6, 8, 12, and 18 x cnl3 mole-' for the C, Si, Ge, Sn, and Pb-carbon bonds respectively. The signals for the vinyl protons of the &MVi series are all located to low field relative to the MVi, series. This deshielding is satisfactorily accounted for by the effects of the phenyl ring diamagnetic anisotropy in the former series.A linear correlation is observed between the sums of the coupling constants and the electronegativities, Em, of the central M atom for both series of compounds. However, the XJvalues for the &MVi series are all slightly lower than the corresponding s u n~s for the MVi4 series, indicating that the electronegativity of the phenyl group is somewhat larger than for the vinyl group.A significant solvent and concentration dependence is only noted for compounds belonging to the &MVi series. For examplc, the tratis proton of +3GeVi shifts up-field by 4 Hz while the cis proton is displaced down-field by 4 Hz as the concentration of 4,GeVi is increased to 50 mole % in carbon tetrachloride. These changes have been interpreted on the basis of a solute-solute interaction scheme of the type proposed previously for phenyl proton shifts.

show abstract

Proton magnetic resonance spectra of tetravinyltin and tetraallyltin: dx-px bonding

Cited by 25 publications

References 17 publications

π-Bonding between C=C bonds and tin in alkenyltin compounds

π-Bonding between C=C bonds and tin in alkenyltin compounds

Electron-transfer polymers. XXXV. Inductive effects of substituents upon spectral and redox properties of p-benzoquinones

Proton magnetic resonance spectra of vinylmetallic compounds. Part I. Tetravinyl and triphenylvinyl derivatives of Group IVB elements

Contact Info

Product

Resources

About