Reaction of ketoximes with aliphatic aldehydes and diphenylborinic acid. Crystal and molecular structure of a diphenylboron chelate derived from the pivaldehyde adduct to cyclohexanone oxime

1998 ◽  
Vol 76 (12) ◽  
pp. 1789-1795 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Ulf Riebe ◽  
Steven J Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Oxygen Atom ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Cyclohexanone Oxime ◽  
Bulky Substituent ◽  
Aliphatic Aldehydes ◽  
Full Matrix ◽  
Diphenylboron Chelate

Various ketoximes have been reacted with aliphatic aldehydes in the presence of oxybis(diphenylborane) in order to assess the influence of increasingly bulky residues on the nature of the products. Crystals of 5-tert-butyl-2-cyclohexylidene-3,3-diphenyl-1,4-dioxa-2-azonia-3-boratacyclopentane, 4c, are monoclinic, a = 14.0647(9), b = 11.416(1), c = 14.756(1) Å, β = 115.696(4)°, Z = 4, space group P21/c. The structure was solved by direct methods and refined by full-matrix least-squares procedures to R = 0.038 (Rw = 0.038) for 2511 reflections with I >= 3σ(I). A bulky substituent at the aldehyde favors α-hydroxyalkylation at the oxime oxygen atom and subsequently leads to the formation of BOCON diphenylboron chelates, whereas formaldehyde reacts by N-alkylation of the oximes, resulting in COBON diphenylboron chelates.Key words: ketoximes, organoboron compounds, crystal structure.

Reaction of N,N′-dihydroxy-.N,N′-dimethylmethanediamine with phenylboronic acid and the crystal and molecular structure of N,N′-dihydroxy-N,N′-dimethylmethanediamine

1989 ◽  
Vol 67 (11) ◽  
pp. 1959-1963 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Least Squares ◽  
Crystal And Molecular Structure ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Exact Formula ◽  
Full Matrix ◽  
Space Group ◽  
Hydrogen Bonded

The reaction of N,N′-dihydroxy-N,N′-dimethylmethanediamine with phenylboronic acid leads to the product 1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane rather than the expected product 1,5-dimethyl-3-phenyl-1,5-diaza-2,4-dioxa-3-boracyclohexane. The structure of N,N′-dihydroxy-N,N′-dimethylmethanediamine has been determined and is discussed in terms of its reaction with PhB(OH)2. Crystals of N,N′-dihydroxy-N,N′-dimethylmethanediamine are tetragonal, a = 8.5346(3), c = 8.4178(7) Å, Z = 4, space group P421c. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.036 and Rw of 0.038 for 333 reflections with I ≥ 3σ(I). The structure consists of hydrogen-bonded dimers having exact [Formula: see text] symmetry. Keywords: N,N′-dihydroxy-N,N′-dimethylmethanediamine, crystal structure.

Crystal and molecular structure of L-prolinatodiphenylboron

1977 ◽  
Vol 55 (6) ◽  
pp. 958-965 ◽  
Author(s):  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Least Squares ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Conformational Disorder ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths

Crystals of L-prolinatodiphenylboron are monoclinic, a = 5.9427(5), b = 14.4633(7), c = 8.9654(4) Å, β = 98.423(8)°, Z = 2, space group P21. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.037 and Rw of 0.053 for 1477 reflections with I ≥ 3σ(I). The proline ring exhibits conformational disorder. The crystal structure consists of discrete molecules linked by N—H … O hydrogen bonds (N … O = 2.893(3) Å) along the short a axis. Intramolecular N—B coordination occurs to form a system of two fused five-membered rings. Bond lengths (corrected for libration) are: N—B, 1.630(3), O—B, 1.529(3), O—C, 1.219(3) and 1.300(3), N—C, 1.506(3) and 1.507(3), C(sp3)–C(sp3), 1.525(4), C(sp2)—C(sp3), 1.517(3), and mean C—C(phenyl), 1.394 Å.

Structural studies of organoboron compounds. XXII. Preparation and crystal and molecular structure of tetramethylammonium-2,4,6,6-tetraphenyl-1,3,5-trioxa-2,4- dibora-6-boratacyclohexane

1985 ◽  
Vol 63 (12) ◽  
pp. 3516-3520 ◽  
Author(s):  
W. Kliegel ◽  
H.-W. Motzkus ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Physical Properties ◽  
Crystal And Molecular Structure ◽  
Structural Parameters ◽  
Direct Methods ◽  
Maximum Deviation ◽  
Structural Studies ◽  
Full Matrix ◽  
The Mean

Details of the preparation and physical properties of (Me4N)+ (Ph4B3O3)− are given. Crystals of tetramethylammonium 2,4,6,6-tetraphenyl-1,3,5-trioxa-2,4-dibora-6-boratacyclohexane are orthorhombic, a = 18.130(2), b = 11.9745(7), c = 12.5187(5) Å, Z = 4, space group Pna21. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.056 and Rw = 0.064 for 1460 reflections with I ≥ 2σ(I). The crystal structure consists of discrete tetramethylammonium cations and tetraphenylboroxinate anions, the first such anion to be structurally characterized. The six-membered B3O3 ring is significantly non-planar, having a flattened O(1)-envelope conformation (maximum deviation from the mean plane = 0.074(4) Å for O(1)). The boroxine ring in the anion shows significant deviations from the D3h symmetry observed for neutral boroxines. Important mean structural parameters: B(sp3)—O = 1.494(2), B(sp2)—O[B(sp3)] = 1.320(9), B(sp2)—O[B(sp2)] = 1.389(3) Å, O—B(sp3)—O = 110.5(5), O—B(sp2)—O = 121.7(6), B(sp2)—O—B(sp2) = 118.9(5), and B(sp3)—O—B(sp2) = 122.9(1)°.

Crystal and molecular structure of 8,8-dimethyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boranatabicyclo[3.3.0]octane

1976 ◽  
Vol 54 (20) ◽  
pp. 3142-3151 ◽  
Author(s):  
Steven J. Rettig ◽  
James Trotter ◽  
W. Kliegel ◽  
H. Becker
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Boron Atom ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
The Other ◽  
Full Matrix ◽  
Atom Bond ◽  
Tetrahedral Boron

Crystals of 8,8-dimethyl-3,5-diphenyl-2,4,6-trioxa-1-azonia-3-bora-5-boranatabicyclo[3.3.0]-octane are monoclinic, a = 22.323(1), b = 9.555(1), c = 16.0027(6) Å, β = 109.055(4)°, Z = 8, space group C2/c. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.048 and Rw of 0.066 for 2629 reflections with I ≥ 3σ(I). The central part of the molecule consists of two fused five-membered rings. One of them is a familiar BOCCN ring while the other is a novel and nearly planar BOBON ring containing one tetrahedral boron atom and one trigonal planar boron atom. Bond lengths are: O—B, 1.337(2)–1.467(2), N—B, 1.692(2), O—N, 1.440(2), O—C, 1.426(2), N—C, 1.513(2), B—C, 1.557(2) and 1.599(2), C(sp3)—C(sp3), 1.520(2)–1.530(2), C—C(ar), 1.372(4)–1.407(2), N—H, 0.89(2), mean C(ar)—H, 0.97(1), and mean C(sp3)—H, 1.01(1) Å. The crystal structure consists of discrete molecules each linked to two others by N—H … O hydrogen bonds (N … O = 2.853(2) Å).

Crystal and Molecular Structure of B-Phenyl-diptychboroxazolidine,

1975 ◽  
Vol 53 (10) ◽  
pp. 1393-1401 ◽  
Author(s):  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Least Squares ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Thermal Motion ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths

Crystals of B-phenyl-dictychboroxazolidine are monoclinic, a = 8.4977(4), b = 9.0617(5), c = 7.0105(3) Å, β = 111.627(3)°, Z = 2, space group P21. The structure was solved by direct methods and was refined by full-matrix least squares procedures to a final R of 0.040 for 967 reflections with I ≥ 3σ(I). The bond lengths involving nonhydrogen atoms have been corrected for thermal motion. Bond lengths are: B—O, 1.460(3) and 1.474(3), B—N, 1.666(3), B—C, 1.613(3), C—O, 1.411(3) and 1.419(3), C—N, 1.485(3) and 1.486(3), C(sp3)—C(sp3), 1.514(4) and 1.524(4), C—C(ar), 1.384–1.400(4–6), mean C—H, 0.98(4), and N—H, 0.87(5) Å. The crystal structure consists of discrete molecules of B-phenyl-diptychboroxazolidine each linked to two others by N—H … O hydrogen bonds (O … N = 2.914(3) Å) to form continuous spirals along b.

Crystal and Molecular Structure of (±)-7,7-(2′,2′-Dimethyl)pentamethylene-1-methyl-norbornane-2-oxime

1975 ◽  
Vol 53 (5) ◽  
pp. 765-776 ◽  
Author(s):  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Least Squares ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Full Matrix ◽  
Space Group ◽  
Centrosymmetric Dimers

Crystals of (±)-7,7-(2′,2′-dimethyl)pentamethylene-1-methyl-norbornane-2-oxime are monoclinic, a = 9.202(2), b = 12.852(3), c = 12.698(3) Å, β = 110.83(2)°, Z = 4, space group P21/c. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.048 for 1538 reflections with I ≥ 3σ(I). The crystal structure consists of pairs of molecules linked by N … H—O hydrogen bonds (N … O = 2.821(3) Å ) to form centrosymmetric dimers. Bond distances are as follows: C—N = 1.266(3), N—O = 1.426(3), mean C(sp3)—C(sp3) = 1.540, and mean C(sp3)—C(sp3) = 1.511 Å.

Crystal and molecular structure of unsubstituted and p-methoxy-substituted acetylbenzoylmethanatoboron difluoride

1997 ◽  
Vol 212 (5) ◽  
Author(s):  
Y. Dromzée ◽  
J. Kossanyi ◽  
V. Wintgens ◽  
P. Valat ◽  
H. Hartmann ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Least Squares ◽  
Crystal Structures ◽  
Structure Analysis ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Crystal Structure Analysis ◽  
Full Matrix

AbstractThe crystal structures of two borines were solved by direct methods and refined by full-matrix least-squares procedure. 6-methyl-4-phenyl-1,3,2-(2The crystal structure analysis of compound

Crystal and Molecular Structure of 2-Deacylusnic Acid

1974 ◽  
Vol 52 (5) ◽  
pp. 723-733 ◽  
Author(s):  
Alistair L. Macdonald ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Structural Feature ◽  
Absolute Configuration ◽  
Title Compound ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Anomalous Scattering ◽  
Full Matrix

Crystals of the title compound are monoclinic a = 9.801(2) b = 9.120(1) c = 8.026(2) Å, β = 107.45(1)°, Z = 2, space group P21. The structure was determined by direct methods, and refined by electron-density and full-matrix least-squares procedures to R = 0.0325 for 1363 observed reflections. An attempt to determine the absolute configuration by use of the anomalous scattering of oxygen and carbon atoms has been made. The most important structural feature is delocalization in the cyclohexadiene ring. There are two intramolecular O—H … O hydrogen bonds, O … O distances 2.532(3) and 2.712(2) Å. The crystal structure consists of molecules linked by intermolecular O—H … O hydrogen bonds, O … O = 2.625(2)Å, to form continuous spirals about the 21 axes.

The Crystal and Molecular-Structure of 4,7,13-Trioxa-1,10-diazacyclopentadecanepotassium(I) Thiocyanate

1988 ◽  
Vol 41 (9) ◽  
pp. 1363 ◽  
Author(s):  
A Abouhamdan ◽  
SF Lincoln ◽  
MR Snow ◽  
ERT Tiekink
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Title Compound ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Monoclinic Space Group ◽  
Compound K ◽  
Unit Cell Parameters ◽  
Full Matrix ◽  
Cell Parameters

The crystal structure of the title compound [K(-NHCH2CH2OCH2CH2OCH2CH2NHCH2CH2OCH2CH2-)(NCS)] has been determined. Potassium(I) is 1.41 Ǻ above the plane of the three oxygens of the 4,7,13-trioxa-1,10-diazacyclopentadecane ligand, and is seven-coordinated. Potassium(I) is 2.871(7), 2.798(7) and 2.772(7)Ǻ from the three oxygens, and 2.905(8) and 2.945(8)Ǻ from the two nitrogens of 4,7,13-trioxa-1,10-diazacyclopentadecane, 2.861(7)Ǻ from an oxygen of a second such ligand, and 2.809(8)Ǻ from the thiocyanate nitrogen. Crystals are monoclinic, space group P21/n with unit cell parameters a 8.015(4), b 14.755(4), c 13.744(4)Ǻ, β 95.37(3)°, and Z 4. The structure was solved by direct methods and refined by a full-matrix least-squares procedure to final R 0.089, Rw 0.099 for 981 reflections with I ≥ 2.5σ(I).

Crystal and molecular structure of B,B-bis(p-tolyl)boroxazolidine and the orthorhombic form of B,B-diphenylboroxazolidine

1976 ◽  
Vol 54 (20) ◽  
pp. 3130-3141 ◽  
Author(s):  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Molecular Structure ◽  
Statistical Analysis ◽  
Hydrogen Bonds ◽  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Length Variation ◽  
Full Matrix ◽  
Space Group ◽  
Phenyl Rings ◽  
Related Compounds

Crystals of B,B-bis(p-tolyl)boroxazolidine, 1c, are trigonal, a = 25.1028(9), c = 12.4184(7) Å, Z = 18, space group [Formula: see text]. And crystals of B,B-diphenylboroxazolidine, 1a, are orthorhombic, a = 17.6420(4), b = 14.2527(3), c = 10.205(1) Å, Z = 8, space group Pbca. Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to final R values of 0.057 and 0.040 for 2230 and 1828 reflections with I ≥ 3σ(I) respectively. Both molecules have structures similar to related compounds and feature intermolecular N—H … O hydrogen bonds (N … O = 2.982(2) for 1c and 2.896(2) Å for 1a). Bond lengths are: for 1c; O—C, 1.413(3), O—B, 1.478(3), N—C, 1.488(3), N—B, 1.657(3), C(sp3)—C(sp3), 1.501(4), B—C, 1.616(3) and 1.623(3), mean C—C(ar), 1.395, N—H, 0.93(2) and 0.94(2), mean C(sp3)—H, 1.00, and mean C(ar)—H, 1.00 Å; for 1a; O—C, 1.409(2), O—B, 1.476(2), N—C, 1.489(2), N—B, 1.655(2), C(sp3)—C(sp3), 1.507(3), B—C, 1.613(2) and 1.620(2), mean C—C(ar), 1.391, N—H, 0.93(2) and 0.92(2), mean C(sp3)—H, 1.00, and mean C(ar)—H, 0.98 Å. A statistical analysis of the phenyl C—C distances in compounds 1a, 1b, and 1c has provided an example of statistically significant substituent-induced bond length variation in the phenyl rings.

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