The structures of 1-, 2- and 3-pyrroline

Boggs, James E.; Kim, Mi Gyung

doi:10.1016/0166-1280(85)87005-6

Cited by 12 publications

(8 citation statements)

References 18 publications

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“…Our MP2 / 6-311+ G ‫ءء‬ calculations, performed with a larger basis set than previously reported, [8][9][10][11][12] predict ⌬E EQ-AX = 259 cm −1 . Our MP2 / 6-311+ G ‫ءء‬ calculations, performed with a larger basis set than previously reported, [8][9][10][11][12] predict ⌬E EQ-AX = 259 cm −1 .…”

Section: Resultsmentioning

confidence: 61%

The ultraviolet photodissociation of axial and equatorial conformers of 3-pyrroline

Oliver

King

Ashfold

2010

The Journal of Chemical Physics

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Resolved sets of photoproducts arising from the photodissociation of axial and equatorial conformers of 3-pyrroline have been observed using H(Rydberg) atom photofragment translational spectroscopy following excitation in the wavelength range of 250-213 nm. 3-pyrroline (alternatively 2,5-dihydropyrrole) is a five membered partially saturated heterocycle in which the bonding around the N atom is pyramidal (sp(3) hybridized) and the N-H bond can lie either axial or equatorial to the ring. Careful analysis of total kinetic energy release data derived from H atom time-of-flight measurements reveals excitation of the 3-pyrrolinyl cofragment consistent with N-H bond fission in both the axial and equatorial conformers. This allows determination of the energy difference between the ground state conformers to be 340±50 cm(-1) and the N-H bond strength for axial and equatorial conformers as 31,610±50 and 31,270±50 cm(-1), respectively.

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Section: Resultsmentioning

confidence: 61%

The ultraviolet photodissociation of axial and equatorial conformers of 3-pyrroline

Oliver

King

Ashfold

2010

The Journal of Chemical Physics

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“…Its structure is depicted in Fig. 1 with dropyrrole prompted ab initio calculations by Boggs and the definition of the angle a for the amino group inversion Kim (4). These authors pointed out that the interpretation coordinate and of the angle b for the ring puckering coor-of the far-infrared spectrum of 2,5-dihydropyrrole leading dinate.…”

Section: Introductionmentioning

confidence: 98%

Microwave and Infrared Spectra,ab InitioCalculation, and Two-Dimensional Model of Amino Group Inversion and Ring Puckering in 2,5-Dihydropyrrole

Dommen¹,

Camináti²,

Hollenstein³

et al. 1996

Journal of Molecular Spectroscopy

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“…The translocation of the allyl proton would originate an allyl anion ( C ), thus accounting for the isomerization of the double bond . The protonation of C would lead to 3-pyrroline 7a since 3-pyrrolines are more stable than 2-pyrrolines . The retro-Claisen reaction on 3-pyrroline 7a would yield the debenzoylated 3-pyrroline 10 (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

Post-Ugi Transformations for the Access to Pyrrolobenzodiazepine Scaffolds with Different Degrees of Unsaturation

et al. 2020

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The synthesis of three novel families of pyrrolo[2,1-c][1,4]benzodiazepine-5-ones is described. The compounds were prepared according to a three-step sequence, involving an Ugi reaction, building of the pyrrolo nucleus and reduction-cyclisation to the corresponding diazepine. Depending on the amine employed in the synthesis of the Ugi adducts, different unsaturation degrees could be obtained in the pyrrolo ring (saturated or with endo or exo unsaturations), a key feature determining their biological activity, as it affected the affinity of the pyrrolobenzoadiazepines towards DNA and thus their cytotoxicity. This synthetic methodology represents a significant improvement with respect to those described in the literature so far, as it uses inexpensive and commercially-available starting materials without needing derivatization or the use of protecting groups.

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The structures of 1-, 2- and 3-pyrroline

Cited by 12 publications

References 18 publications

The ultraviolet photodissociation of axial and equatorial conformers of 3-pyrroline

The ultraviolet photodissociation of axial and equatorial conformers of 3-pyrroline

Microwave and Infrared Spectra,ab InitioCalculation, and Two-Dimensional Model of Amino Group Inversion and Ring Puckering in 2,5-Dihydropyrrole

Post-Ugi Transformations for the Access to Pyrrolobenzodiazepine Scaffolds with Different Degrees of Unsaturation

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