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The effect of the nitrogen non-bonding electron pair on the NMR and X-ray in 1,3-diazaheterocycles

The effect of the nitrogen nonbonding electron pair on the 1JC,H values of 1,3-diazaheterocycles was analyzed and compared to 1,5-diazabiciclo[3.2.1]octanes, which have a restricted conformation. The 1JC,H values were measured by observing the 13C satellites in the 1H NMR spectra and then determinin... Full description

Journal Title: Tetrahedron Letters 20120627, Vol.53(26), pp.3310-3315
Main Author: Garcias-Morales, Cesar
Other Authors: Martinez-Salas, Selene , Ariza-Castolo, Armando
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0040-4039 ; DOI: 10.1016/j.tetlet.2012.04.077
Link: http://search.proquest.com/docview/1744679465/?pq-origsite=primo
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title: The effect of the nitrogen non-bonding electron pair on the NMR and X-ray in 1,3-diazaheterocycles
format: Article
creator:
  • Garcias-Morales, Cesar
  • Martinez-Salas, Selene
  • Ariza-Castolo, Armando
subjects:
  • Tetrahedrons
  • X-Rays
  • Orbitals
  • Satellite Observation
  • Nuclear Magnetic Resonance
  • Spectra
  • Satellites
  • Miscellaneous Sciences (So)
  • Chemical and Electrochemical Properties (MD)
  • Chemical and Electrochemical Properties (Ep)
  • Chemical and Electrochemical Properties (Ed)
  • Chemical and Electrochemical Properties (EC)
  • Stereoelectronic Effect
  • Nonbonding Electron Pair
  • Spinaspin Coupling Constant
  • X-Ray Structure
  • Homohyperconjugation
ispartof: Tetrahedron Letters, 20120627, Vol.53(26), pp.3310-3315
description: The effect of the nitrogen nonbonding electron pair on the 1JC,H values of 1,3-diazaheterocycles was analyzed and compared to 1,5-diazabiciclo[3.2.1]octanes, which have a restricted conformation. The 1JC,H values were measured by observing the 13C satellites in the 1H NMR spectra and then determining the 1H-coupled 13C NMR spectra. The 1JC,H values are 10 Hz larger when the [alpha]-hydrogen is synperiplanar rather than antiperiplanar to the nonbonding electron pair on the nitrogen, which serves as experimental evidence of the orbital nNaIaC,Hap interactions. In addition, the homoanomeric effect from the interactions of the nitrogen lone pair with the antibonding orbital of the equatorial hydrogen, which was in the I2 position, was discussed (nNaIaC(I2),Heq).
language: eng
source:
identifier: ISSN: 0040-4039 ; DOI: 10.1016/j.tetlet.2012.04.077
fulltext: fulltext
issn:
  • 00404039
  • 0040-4039
url: Link


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titleThe effect of the nitrogen non-bonding electron pair on the NMR and X-ray in 1,3-diazaheterocycles
creatorGarcias-Morales, Cesar ; Martinez-Salas, Selene ; Ariza-Castolo, Armando
contributorGarcias-Morales, Cesar (correspondence author)
ispartofTetrahedron Letters, 20120627, Vol.53(26), pp.3310-3315
identifierISSN: 0040-4039 ; DOI: 10.1016/j.tetlet.2012.04.077
subjectTetrahedrons ; X-Rays ; Orbitals ; Satellite Observation ; Nuclear Magnetic Resonance ; Spectra ; Satellites ; Miscellaneous Sciences (So) ; Chemical and Electrochemical Properties (MD) ; Chemical and Electrochemical Properties (Ep) ; Chemical and Electrochemical Properties (Ed) ; Chemical and Electrochemical Properties (EC) ; Stereoelectronic Effect ; Nonbonding Electron Pair ; Spinaspin Coupling Constant ; X-Ray Structure ; Homohyperconjugation
descriptionThe effect of the nitrogen nonbonding electron pair on the 1JC,H values of 1,3-diazaheterocycles was analyzed and compared to 1,5-diazabiciclo[3.2.1]octanes, which have a restricted conformation. The 1JC,H values were measured by observing the 13C satellites in the 1H NMR spectra and then determining the 1H-coupled 13C NMR spectra. The 1JC,H values are 10 Hz larger when the [alpha]-hydrogen is synperiplanar rather than antiperiplanar to the nonbonding electron pair on the nitrogen, which serves as experimental evidence of the orbital nNaIaC,Hap interactions. In addition, the homoanomeric effect from the interactions of the nitrogen lone pair with the antibonding orbital of the equatorial hydrogen, which was in the I2 position, was discussed (nNaIaC(I2),Heq).
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titleThe effect of the nitrogen non-bonding electron pair on the NMR and X-ray in 1,3-diazaheterocycles
descriptionThe effect of the nitrogen nonbonding electron pair on the 1JC,H values of 1,3-diazaheterocycles was analyzed and compared to 1,5-diazabiciclo[3.2.1]octanes, which have a restricted conformation. The 1JC,H values were measured by observing the 13C satellites in the 1H NMR spectra and then determining the 1H-coupled 13C NMR spectra. The 1JC,H values are 10 Hz larger when the [alpha]-hydrogen is synperiplanar rather than antiperiplanar to the nonbonding electron pair on the nitrogen, which serves as experimental evidence of the orbital nNaIaC,Hap interactions. In addition, the homoanomeric effect from the interactions of the nitrogen lone pair with the antibonding orbital of the equatorial hydrogen, which was in the I2 position, was discussed (nNaIaC(I2),Heq).
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titleThe effect of the nitrogen non-bonding electron pair on the NMR and X-ray in 1,3-diazaheterocycles
authorGarcias-Morales, Cesar ; Martinez-Salas, Selene ; Ariza-Castolo, Armando
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abstractThe effect of the nitrogen nonbonding electron pair on the 1JC,H values of 1,3-diazaheterocycles was analyzed and compared to 1,5-diazabiciclo[3.2.1]octanes, which have a restricted conformation. The 1JC,H values were measured by observing the 13C satellites in the 1H NMR spectra and then determining the 1H-coupled 13C NMR spectra. The 1JC,H values are 10 Hz larger when the [alpha]-hydrogen is synperiplanar rather than antiperiplanar to the nonbonding electron pair on the nitrogen, which serves as experimental evidence of the orbital nNaIaC,Hap interactions. In addition, the homoanomeric effect from the interactions of the nitrogen lone pair with the antibonding orbital of the equatorial hydrogen, which was in the I2 position, was discussed (nNaIaC(I2),Heq).
doi10.1016/j.tetlet.2012.04.077
urlhttp://search.proquest.com/docview/1744679465/
eissn18733581
date2012-06-27