XRD and VCD: a marriage of love or convenience? Honeymoon around a cyclic urea derivative

Gherase, Dragoş; Naubron, Jean-Valère; Roussel, Christian; Giorgi, Michel

doi:10.1107/s010827011202358x

Cited by 4 publications

(2 citation statements)

References 19 publications

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“…Even though chiroptical spectroscopic methods have become highly popular, it has been demonstrated that it is important to use more than one method for determining the structure of chiral molecules . Therefore, in our problem pertinent information concerning chirality had to be inferred from the cooperative use of both XRD and VCD …”

Section: Introductionmentioning

confidence: 99%

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Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements

et al. 2013

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The absolute configurations (AC) of azaheterocylic compounds resulting from the cascade rearrangement of enediynes involving only light atoms were unambiguously assigned by the joint use of vibrational circular dichroism (VCD) and copper radiation single crystal X-ray diffraction (XRD). These AC determinations proved that the rearrangements of enediynes proceeded with memory of chirality and retention of configuration.

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Section: Introductionmentioning

confidence: 99%

“…22 Therefore, in our problem pertinent information concerning chirality had to be inferred from the cooperative use of both XRD and VCD. 23 We report herein how the combination of both techniques was used to demonstrate that the rearrangement of enediynes, including only light atoms, proceeded as assumed with retention of configuration.…”

Section: Introductionmentioning

confidence: 99%

Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements

et al. 2013

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Investigation of Steric Influences on Hydrogen‐Bonding Motifs in Cyclic Ureas by Using X‐Ray, Neutron, and Computational Methods

McCormick

McDonnell-Worth

Platts

et al. 2013

Chemistry An Asian Journal

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A series of urea-derived heterocycles, 5N-substituted hexahydro-1,3,5-triazin-2-ones, has been prepared and their structures have been determined for the first time. This family of compounds only differ in their substituent at the 5-position (which is derived from the corresponding primary amine), that is, methyl (1), ethyl (2), isopropyl (3), tert-butyl (4), benzyl (5), N,N-(diethyl)ethylamine (6), and 2-hydroxyethyl (7). The common heterocyclic core of these molecules is a cyclic urea, which has the potential to form a hydrogen-bonding tape motif that consists of self-associative R₂²(8) dimers. The results from X-ray crystallography and, where possible, Laue neutron crystallography show that the hydrogen-bonding motifs that are observed and the planarity of the hydrogen bonds appear to depend on the steric hindrance at the α-carbon atom of the N substituent. With the less-hindered substituents, methyl and ethyl, the anticipated tape motif is observed. When additional methyl groups are added onto the α-carbon atom, as in the isopropyl and tert-butyl derivatives, a different 2D hydrogen-bonding motif is observed. Despite the bulkiness of the substituents, the benzyl and N,N-(diethyl)ethylamine derivatives have methylene units at the α-carbon atom and, therefore, display the tape motif. The introduction of a competing hydrogen-bond donor/acceptor in the 2-hydroxyethyl derivative disrupts the tape motif, with a hydroxy group interrupting the N-H···O=C interactions. The geometry around the hydrogen-bearing nitrogen atoms, whether planar or non-planar, has been confirmed for compounds 2 and 5 by using Laue neutron diffraction and rationalized by using computational methods, thus demonstrating that distortion of O-C-N-H torsion angles occurs to maintain almost-linear hydrogen-bonding interactions.

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FT-Raman, FT-IR and UV–visible spectral investigations and ab initio computations of anti-epileptic drug: Vigabatrin

Edwin¹,

Joe²

2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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XRD and VCD: a marriage of love or convenience? Honeymoon around a cyclic urea derivative

Cited by 4 publications

References 19 publications

Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements

Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements

Investigation of Steric Influences on Hydrogen‐Bonding Motifs in Cyclic Ureas by Using X‐Ray, Neutron, and Computational Methods

FT-Raman, FT-IR and UV–visible spectral investigations and ab initio computations of anti-epileptic drug: Vigabatrin

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