Polar Assembly of <i>N</i>,<i>N</i>‘-Bis(4-substituted benzyl)sulfamides

Gong, Bing; Zheng, Chong; Zeng, Huaqiang; Zhu, Jin

doi:10.1021/ja992432j

Cited by 49 publications

(17 citation statements)

References 26 publications

(16 reference statements)

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“…Both (3) and (4) contain chiral layers and, interestingly, these layers are formed from achiral building units. This is somewhat analogous to certain organic compounds, where also achiral molecules are able to form chiral layers (Tanaka et al, 2006;Gong et al, 1999). Within the concept of such an interpretation the structure of (3) can then be described as a racemate consisting of two A and A 0 chiral layers which are mirror images of each other reflected in the ac plane.…”

Section: To Both Upper and Lowermentioning

confidence: 94%

Formation of co-racemic uranyl chromate constructed from chiral layers of different topology

Siidra

Nazarchuk

Bocharov

et al. 2017

Acta Crystallogr Sect B

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4). Their structures are based on two-dimensional chiral or achiral units with the composition [(UO 2 ) 2 (CrO 4 ) 3 (H 2 O)] 2À and two types of topologies (A or/and B). The structural architecture of (4) is unique amongst all known uranyl-based structures, and unusual among hybrid organic/inorganic structures in general as it contains layers of identical composition, but of different topology. The unique structural configurations and non-centrosymmetry in (1) and (4) is governed by selective formation of hydrogen bonding rather than by the formation of hydrophobic and hydrophilic zones in the organic interlayer. It is shown that chiral architectures in uranyl systems may form from achiral building units as observed in (3) and (4). This is somewhat analogous to certain organic compounds, where achiral molecules are also able to form chiral layers. Within the concept of such an interpretation the structure of (3) can then be described as a racemate consisting of two A and A 0 chiral layers. In a similar approach the structure of (4) can be interpreted as being formed by four chiral layers. Layer pairs AA 0 and BB 0 can then be considered as racemic pairs and the whole structure is a co-racemate built by a combination of two racemates. Two-stage formation can be suggested for (4).

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Section: To Both Upper and Lowermentioning

confidence: 94%

Formation of co-racemic uranyl chromate constructed from chiral layers of different topology

Siidra

Nazarchuk

Bocharov

et al. 2017

Acta Crystallogr Sect B

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“…The sulfamide functionality with R 2 NSO 2 NR’ 2 structure can be found in several biorelevant compounds [ 21 ]. Besides applications in medicinal chemistry, sulfamide groups have been incorporated in self-assembling molecules [ 22 – 27 ], peptides [ 28 ], polymers [ 29 ], ligands [ 30 ], chiral auxiliaries [ 31 – 33 ] and in organocatalysts [ 34 – 37 ]. In light of the importance of the sulfamide functionality, our group has recently reported a straightforward preparation of unsymmetrical sulfamides from commercially available amines and N -hydroxyarenesulfonamide O -derivatives under simple conditions [ 38 – 39 ].…”

Section: Introductionmentioning

confidence: 99%

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

Pantaine¹,

Humblot²,

Coeffard³

et al. 2017

Beilstein J. Org. Chem.

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Aniline-terminated self-assembled monolayers (SAMs) on gold surfaces have successfully reacted with ArSO2NHOSO2Ar (Ar = 4-MeC6H4 or 4-FC6H4) resulting in monolayers with sulfamide moieties and different end groups. Moreover, the sulfamide groups on the SAMs can be hydrolyzed showing the partial regeneration of the aniline surface. SAMs were characterized by water contact angle (WCA) measurements, Fourier-transform infrared reflection absorption spectroscopy (IRRAS) and X-ray photoelectron spectroscopy (XPS).

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“…The formation of chiral crystals from achiral compounds has attracted much attention because chemical reactions of achiral compounds under asymmetric conditions can lead to absolute asymmetric synthesis,1 which could be the key to the origin of homochirality of life 2. Some chiral systems are known in the solid state, in which robust supramolecular motifs, such as hydrogen‐bonded networks and π–π stacking, are adopted to obtain chiral crystals with helical1e, 3 and layered structures 4. However, even in these sophisticated supramolecular systems the nature of the relationship between the molecular structures and the appearance of supramolecular chirality5 in the crystals still remains ambiguous.…”

mentioning

confidence: 99%

Supramolecular Chirality in Layered Crystals of Achiral Ammonium Salts and Fatty Acids: A Hierarchical Interpretation

et al. 2006

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Polar Assembly of N,N‘-Bis(4-substituted benzyl)sulfamides

Cited by 49 publications

References 26 publications

Formation of co-racemic uranyl chromate constructed from chiral layers of different topology

Formation of co-racemic uranyl chromate constructed from chiral layers of different topology

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

Supramolecular Chirality in Layered Crystals of Achiral Ammonium Salts and Fatty Acids: A Hierarchical Interpretation

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