An official website of the United States government
The title compound, C 10 H 13 NO 2 S, was synthesized by a nucleophilic substitution reaction between allyl amine and p -toluenesulfonyl chloride. The sulfonate S—O bond lengths are 1.4282 (17) and 1.4353 (17) Å, and the C—N—S—C torsion angle involving the sulfonamide moiety is −61.0 (2)°. In the crystal, centrosymmetric dimers of the title compound are present via intermolecular N—H...O hydrogen bonds between sulfonamide groups. These dimers are linked into ribbons along the c -axis direction through offset π–π interactions.
more »
« less
Synthesis and crystallographic characterization of N-allyl-N-benzyl-4-methylbenzenesulfonamide
N-Benzyl-4-methylbenzenesulfonamides were prepared via a two-step synthetic process involving the treatment of 4-methylbenzenesulfonyl chloride with a primary amine to give the corresponding 4-methylbenzenesulfonamide. Benzylation of the sulfonamide affords the substituted N-benzyl-4-methylbenzenesulfonamides. The similarities between the two steps of synthesis lend credence to the development of a one-pot synthesis of substituted N-benzyl-4-methylbenzenesulfonamides from 4-methylbenzenesulfonyl chloride. This method was applied to the synthesis of N-allyl-N-benzyl-4-methylbenzenesulfonamide and characterized through spectroscopic and crystallographic means. The crystal structure of N-allyl-N-benzyl-4-methylbenzenesulfonamide was obtained by single-crystal X-ray diffraction. The crystal structure reveals an orthorhombic Pna21 space group with cell parameters a = 18.6919 (18) Å, b = 10.5612 (10) Å, c = 8.1065 (8) Å, V = 1600.3 (3) Å3 and Z = 4, T = 173.15 K, μ(MoKα) = 0.206 mm-1, Dcalc = 1.251 g/cm3, 14455 reflections measured (4.36° ≤ 2Θ ≤ 54.96°), 3619 unique (Rint = 0.0439, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0428 (I > 2σ(I)) and wR2 was 0.1079 (all data). Molecules are linked through C-H···N hydrogen bonds and C-H···π interactions.
more »
« less
- PAR ID:
- 10205937
- Date Published:
- Journal Name:
- European Journal of Chemistry
- Volume:
- 11
- Issue:
- 3
- ISSN:
- 2153-2249
- Page Range / eLocation ID:
- 245 to 249
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
-
The synthesis of the title compound, C 13 H 21 NO 2 S, is reported here along with its crystal structure. This compound crystallizes with two molecules in the asymmetric unit. The sulfonamide functional group of this structure features S=O bond lengths ranging from 1.433 (3) to 1.439 (3) Å, S—C bond lengths of 1.777 (3) and 1.773 (4) Å, and S—N bond lengths of 1.622 (3) and 1.624 (3) Å. When viewing the molecules down the S—N bond, the isopropyl groups are gauche to the aromatic ring. On each molecule, two methyl hydrogen atoms of one isopropyl group are engaged in intramolecular C—H...O hydrogen bonds with a nearby sulfonamide oxygen atom. Intermolecular C—H...O hydrogen bonds and C—H...π interactions link molecules of the title compound in the solid state.more » « less
-
Two bis-carbamoylmethylphosphine oxide compounds, namely {[(3-{[2-(diphenylphosphinoyl)ethanamido]methyl}benzyl)carbamoyl]methyl}diphenylphosphine oxide, C 36 H 34 N 2 O 4 P 2 , (I), and diethyl [({2-[2-(diethoxyphosphinoyl)ethanamido]ethyl}carbamoyl)methyl]phosphonate, C 14 H 30 N 2 O 8 P 2 , (II), were synthesized via nucleophilic acyl substitution reactions between an ester and a primary amine. Hydrogen-bonding interactions are present in both crystals, but these interactions are intramolecular in the case of compound (I) and intermolecular in compound (II). Intramolecular π–π stacking interactions are also present in the crystal of compound (I) with a centroid–centroid distance of 3.9479 (12) Å and a dihedral angle of 9.56 (12)°. Intermolecular C—H...π interactions [C...centroid distance of 3.622 (2) Å, C—H...centroid angle of 146°] give rise to supramolecular sheets that lie in the ab plane. Key geometric features for compound (I) involve a nearly planar, trans- amide group with a C—N—C—C torsion angle of 169.12 (17)°, and a torsion angle of −108.39 (15)° between the phosphine oxide phosphorus atom and the amide nitrogen atom. For compound (II), the electron density corresponding to the phosphoryl group was disordered, and was modeled as two parts with a 0.7387 (19):0.2613 (19) occupancy ratio. Compound (II) also boasts a trans -amide group that approaches planarity with a C—N—C—C torsion angle of −176.50 (16)°. The hydrogen bonds in this structure are intermolecular, with a D ... A distance of 2.883 (2) Å and a D —H... A angle of 175.0 (18)° between the amide hydrogen atom and the P=O oxygen atom. These non-covalent interactions create ribbons that run along the b -axis direction.more » « less
-
The crystal structure of the title sulfonamide, C 10 H 15 NO 2 S, comprises two molecules in the asymmetric unit. The S=O bond lengths of the sulfonamide functional group range from 1.428 (2) to 1.441 (2) Å, with S—C bond lengths of 1.766 (3) Å (for both molecules in the asymmetric unit), and S—N bond lengths of 1.618 (2) and 1.622 (3) Å, respectively. When both molecules are viewed down the N—S bond, the propyl group is gauche to the toluene moiety. In the crystal structure, molecules of the title compound are arranged in an intricate three-dimensional network that is formed via intermolecular C—H...O and N—H...O hydrogen bonds. The crystal structure was refined from a crystal twinned by inversion.more » « less
-
N -(5-Cyanononan-5-yl)benzamide, C 17 H 24 N 2 O, synthesized from the reaction between benzoyl chloride and 2-amino-2-butylhexanenitrile, is an important intermediate in amino acid synthesis. Intermolecular N—H...O and C—H...O hydrogen bonds with N...O and C...O distances of 3.083 (2) and 3.304 (2) Å, respectively, link adjacent molecules into chains along the a axis. The dihedral angle between the mean plane of the phenyl group and the plane of the amide group is 19.504 (4)°.more » « less
- Free Publicly Accessible Full Text
-
Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.5155/eurjchem.11.3.245-249.2017
