1989
DOI: 10.1016/0022-328x(89)85246-5
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Molecular and crystal structure of N-(fluorodimethylsilylmethyl)pyrrolidone-2

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Cited by 23 publications
(9 citation statements)
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“…The hydrogen atom in 2f and 2k is rather close to the oxygen atom. This is in marked contrast to the case of the N -(silylmethyl)amides having the electron-withdrawing groups such as fluorine and chlorine on the silyl atom . It is probably because the energy level of the σ* orbital of the silicon−carbon bond is not low enough to interact with the lone-pair electrons on the carbonyl group, and the steric factor may be a dominant factor to control the conformations.…”
Section: Resultsmentioning
confidence: 83%
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“…The hydrogen atom in 2f and 2k is rather close to the oxygen atom. This is in marked contrast to the case of the N -(silylmethyl)amides having the electron-withdrawing groups such as fluorine and chlorine on the silyl atom . It is probably because the energy level of the σ* orbital of the silicon−carbon bond is not low enough to interact with the lone-pair electrons on the carbonyl group, and the steric factor may be a dominant factor to control the conformations.…”
Section: Resultsmentioning
confidence: 83%
“…N -(Silylalkyl)amides: X-ray Molecular Structure Analysis and Hydrolysis. The structures of N -(silylalkyl)amides are of great interest, in particular, whether there is an interaction between the silyl group and the oxygen atom of the carbonyl group or not . After several disappointing results, the single crystal of 2f and N -(1-dimethylphenylsilyl)propylacetamide 2k 5 was successfully obtained.…”
Section: Resultsmentioning
confidence: 99%
“…(b) Part 105: T. K. Prakasha Recently, we have found that sulfur also serves as a donor atom with acyclic (J) 29 and cyclic (K-M) 29,30 oxysilanes in promoting increased coordination toward a trigonal bipyramidal geometry. However, a more narrow range of Si-S ax distances (2.98-3.29 Å) is evident in these derivatives compared to that found for silanes with nitrogen 17-20 and oxygen [23][24][25][26][27][28] acting as donor atoms, i.e., 0.31 Å. Again these Si-S distances are between the covalent 21 and van der Waals 22 sum of 2.20 and 3.90 Å, respectively.…”
Section: Introductionmentioning
confidence: 71%
“…A sampling of the types of silanes studied by X-ray diffraction that incorporate nitrogen donation [17][18][19][20] in Table 1 shows Si-N ax distances ranging from 1.97 to 2.66 Å, well within the limits of a Si-N single bond value (1.93 Å 21 ) and a van der Waals distance (3.65 Å 22 ). Similarly, Table 2 illustrates structural data on a sampling of silanes that have undergone oxygen atom coordination [23][24][25][26][27][28] providing Si-O ax lengths from 1.75 to 2.40 Å, over a similar range of values as exhibited with silanes having nitrogen atom coordination, 0.65 Å for the oxygen series X Abstract published in AdVance ACS Abstracts, May 1, 1996.…”
Section: Introductionmentioning
confidence: 98%
“…Strong coordination in these molecules is also supported by the IR spectra (in KBr) which exhibited the ν(CO) bands at 1603 cm -1 for 3 and 1607 cm -1 for 4 . The ν(CO) of analogous ( 5 ) also appeared at the same region (1598 cm -1 ),7a indicating that replacement of two equatorial methyl groups in 5 by two silyl groups has no influence on the strength of the O−Si bond . This result is somewhat surprising, because the presence of an electropositive ligand such as silicon in the equatorial position is supposed to weaken the coordination bond. ,7c …”
mentioning
confidence: 98%