The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides

Omondi, Bernard; Lemmerer, Andreas; Fernandes, Manuel A.; Levendis, Demetrius C.; Layh, Marcus

doi:10.1039/b820944h

Cited by 5 publications

(12 citation statements)

References 20 publications

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“…The structures of (I)-(V) and (VII) have been reported previously by us (Omondi et al, 2005;Omondi, Lemmerer et al, 2009;Omondi & Levendis, 2012). The structure of (VI) has been reported previously by Chitanda et al (2008).…”

Section: Crystal Structures Of the Starting Materials (I)-(vii)supporting

confidence: 71%

“…The thioamide solid solution (3) also has the trans conformation, while the solid solution formed by superimposing the N-phenylformamide/N-phenylthioamide compounds continues with the trans conformation. Bond distances and angles for all solid solutions show great similarities and compare well to those of other disubstituted Nphenylformamides (Omondi et al, 2005; and N-phenylthioamides (Omondi, Lemmerer et al, 2009). In all of the crystals, the formamide/thioamide moiety is out of the plane of the phenyl ring.…”

Section: Molecular Structures Crystal Structures Intermolecular Intsupporting

confidence: 57%

“…2,6-Disubstituted N-phenylformamides and N-phenylthioamides were synthesized using methods reported previously (Omondi et al, 2005Omondi, Lemmerer et al, 2009;Fernandes & Reid, 2003;Ugi et al, 1965). The starting materials, in a 1:1 stoichiometric ratio of the following: 1 (Ia) and (IIa) for (1), (IIa) and (III) for (2), (IV) and (V) for (3), and (VI) and (VII) for (4), were then dissolved in an appropriate solvent (a single solvent or a mixture that dissolved both ground compounds equally well), The two conformations commonly adopted by the hydrogen-bonded functional group for the formamides and thioamides, in this case shown for the formamide case only.…”

Section: Preparation Of Solid Solutions (1)-(4)mentioning

confidence: 99%

“…In earlier work, we have observed that replacement of Cl and methyl groups in a series of 2,6-disubstituted N-phenylformamides result in isostructural crystal structures, some of which undergo reversible thermal phase transformations (Omondi et al, 2005;. When similar exchanges of substituents were carried out using the analogous thioamides, isostructural crystals could also be isolated (Omondi, Lemmerer et al, 2009).…”

Section: Introductionmentioning

confidence: 97%

“…Importantly, the compounds can exist as either cis or trans isomers, depending on their physical state (liquid or solid; Fig. 2), and have been observed to exist as a mixture of cis and trans isomers in solution (Gowda et al, 2000;Omondi, Lemmerer et al, 2009;Omondi et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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In order to investigate possible isostructural solid solutions of disubstituted N-phenylformamides and thioamides, we have studied the re-crystallization of pairs of compounds selected from 2,6-difluoro-N-phenylformamide (I), 2,6-dichloro-N-phenylformamide (II), 2,6-dimethyl-N-phenylformamide (III), 2,6-dichloro-N-phenylthioamide (IV), 2,6-dimethyl-N-phenylthioamide (V), 2,6-diisopropyl-N-phenylformamide (VI) and 2,6-diisopropyl-N-phenylthioamide (VII). For single-component 2,6-disubstituted-N-phenylformamides only the trans form occurs in the pure crystal, while for thioamides the cis form occurs, with only one exception. By forming solid solutions of pairs of these molecules the resulting structures all adopt similar N-H...O/S chains in the crystals. Solid solutions (1), (2) and (3), resulting from the mixing of (I) and (II), (II) and (III), and (IV) and (V), respectively, are all isostructural with each other (space group Pbca). Only co-crystal (1) is isostructural to both starting materials, while (2) is isostructural to only one of the starting pair, (II). Solid solution (3), which adopts the same Pbca structure as (1) and (2), is different to the monoclinic structures of both the reactants. Solid solution (4) is monoclinic, with similar hydrogen-bonded chains, and isostructural to the two components, resulting from the composition from the mixing of (VI) and (VII). Isostructural indices were used to quantify crystal-packing similarities and differences. Occupancy factors of the reactants in each co-crystal differ widely.

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Section: Crystal Structures Of the Starting Materials (I)-(vii)supporting

confidence: 71%

Section: Molecular Structures Crystal Structures Intermolecular Intsupporting

confidence: 57%

Section: Preparation Of Solid Solutions (1)-(4)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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Two polymorphs ofN-(2,6-difluorophenyl)formamide

et al. 2009

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The structures of two distinct polymorphic forms of N-(2,6-difluorophenyl)formamide, C(7)H(5)F(2)NO, have been studied using single crystals obtained under different crystallizing conditions. The two forms crystallize in different space groups, viz. form (Ia) in the orthorhombic Pbca and form (Ib) in the monoclinic P2(1) space group. Each polymorph crystallizes with one complete molecule in the asymmetric unit and they have a similar molecular geometry, showing a trans conformation with the formamide group being out of the plane of the aromatic ring. The packing arrangements of the two polymorphs are quite different, with form (Ia) having molecules that are stacked in an alternating arrangement, linked into chains of N-H...O hydrogen bonds along the crystallographic a direction, while form (Ib) has its N-H...O hydrogen-bonded molecules stacked in a linear fashion. A theoretical study of the two structures allows information to be gained regarding other contributing interactions, such as pi-pi and weak C-H...F, in their crystal structures.

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N-(2,6-Diisopropylphenyl)thioamide

Omondi

Levendis

2012

Acta Cryst E

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In the crystal structure of the title compound, C13H19NS {systematic name: N-[2,6-bis(propan-2-yl)phenyl]carbothioamide}, molecules assemble via N—H⋯S=C hydrogen bonds into helical chains along the b axis. The thioamide moiety, with a syn disposition of the N- and C-bound H atoms, is twisted out of the plane of the benzene ring to which it is connected, forming a dihedral angle angle of 77.60 (14)°.

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The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides

Cited by 5 publications

References 20 publications

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Two polymorphs ofN-(2,6-difluorophenyl)formamide

N-(2,6-Diisopropylphenyl)thioamide

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