|
|
|
|
| LEADER |
01000naa a22002652 4500 |
| 001 |
NLM294022198 |
| 003 |
DE-627 |
| 005 |
20231225080610.0 |
| 007 |
cr uuu---uuuuu |
| 008 |
231225s2019 xx |||||o 00| ||eng c |
| 024 |
7 |
|
|a 10.1002/mrc.4854
|2 doi
|
| 028 |
5 |
2 |
|a pubmed24n0980.xml
|
| 035 |
|
|
|a (DE-627)NLM294022198
|
| 035 |
|
|
|a (NLM)30776853
|
| 040 |
|
|
|a DE-627
|b ger
|c DE-627
|e rakwb
|
| 041 |
|
|
|a eng
|
| 100 |
1 |
|
|a Silla, Josué M
|e verfasserin
|4 aut
|
| 245 |
1 |
0 |
|a Influence of stereoelectronic effects on the 1 JC─F spin-spin coupling constant in fluorinated heterocyclic compounds
|
| 264 |
|
1 |
|c 2019
|
| 336 |
|
|
|a Text
|b txt
|2 rdacontent
|
| 337 |
|
|
|a ƒaComputermedien
|b c
|2 rdamedia
|
| 338 |
|
|
|a ƒa Online-Ressource
|b cr
|2 rdacarrier
|
| 500 |
|
|
|a Date Completed 17.09.2019
|
| 500 |
|
|
|a Date Revised 17.09.2019
|
| 500 |
|
|
|a published: Print-Electronic
|
| 500 |
|
|
|a Citation Status PubMed-not-MEDLINE
|
| 520 |
|
|
|a © 2019 John Wiley & Sons, Ltd.
|
| 520 |
|
|
|a The Perlin effect and its analog for fluorinated compounds (the fluorine Perlin-like effect) manifest on one-bond C─H (C─F for the fluorine Perlin-like effect) spin-spin coupling constants (SSCCs) in six-membered rings. These effects can be useful to probe the stereochemistry (axial or equatorial) of the C─H and C─F bonds, respectively. The origin of these effects has been debatable in the literature as being due to hyperconjugative interactions, dipolar effects, and induced current density. Accordingly, a variety of model compounds has been used to probe such effects since the cyclohexanone carbonyl group and the endocyclic heteroatom lone pairs play different roles on the above-mentioned effects. Thus, the 1 JC─F SSCC in fluorinated lactams and lactones were theoretically studied to gain further insight on the nature of the fluorine Perlin-like effect. In addition, because the intramolecular α-effect has recently gained attention for its importance in the reactivity and stereoelectronic interactions in peroxide compounds, some fluorinated 1,2-dioxanes and 1,2-dithianes were studied to evaluate the role of the α-effect on the behavior of 1 JC─F SSCCs. Differently from fluorinated ketones and ethers, the fluorine Perlin-like effect in the amides and esters cannot be explained by hyperconjugative or dipolar interactions alone, because the resonance in these groups affect the 1 JC─F values. The O─O and S─S-containing systems exhibit a strong fluorine Perlin-like effect, but unlike the α-effect, this behavior cannot be explained neither by hyperconjugation nor by dipolar interactions alone; the spatial proximity of the C─F and O─O/S─S bonds is proposed to affect the magnitude of the 1 JC─F SSCC
|
| 650 |
|
4 |
|a Journal Article
|
| 650 |
|
4 |
|a Research Support, Non-U.S. Gov't
|
| 650 |
|
4 |
|a dipolar interactions
|
| 650 |
|
4 |
|a fluorine Perlin-like effect
|
| 650 |
|
4 |
|a hyperconjugation
|
| 650 |
|
4 |
|a one-bond C─F coupling constant
|
| 650 |
|
4 |
|a organofluorine compounds
|
| 700 |
1 |
|
|a Andrade, Laize A F
|e verfasserin
|4 aut
|
| 700 |
1 |
|
|a Freitas, Matheus P
|e verfasserin
|4 aut
|
| 773 |
0 |
8 |
|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 57(2019), 7 vom: 18. Juli, Seite 373-379
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
|
| 773 |
1 |
8 |
|g volume:57
|g year:2019
|g number:7
|g day:18
|g month:07
|g pages:373-379
|
| 856 |
4 |
0 |
|u http://dx.doi.org/10.1002/mrc.4854
|3 Volltext
|
| 912 |
|
|
|a GBV_USEFLAG_A
|
| 912 |
|
|
|a SYSFLAG_A
|
| 912 |
|
|
|a GBV_NLM
|
| 912 |
|
|
|a GBV_ILN_350
|
| 951 |
|
|
|a AR
|
| 952 |
|
|
|d 57
|j 2019
|e 7
|b 18
|c 07
|h 373-379
|