Structural studies of organoboron compounds. XXXVI. 2,2-Dimethyl-3,3-diphenyl-1,4-dioxa-2-azonia-3-boratacyclohexane

1989 ◽  
Vol 67 (12) ◽  
pp. 2218-2221 ◽  
Author(s):  
Klaus Drückler ◽  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Least Squares ◽  
Title Compound ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Boron Compound ◽  
Structural Studies ◽  
Organoboron Compounds ◽  
Full Matrix ◽  
Space Group

The synthesis of O-(2-hydroxyethyl)-N,N-dimethylhydroxylamine and its reaction with oxybis(diphenylborane) to yield the title compound are reported. Crystals of 2,2-dimethyl-3,3-diphenyl-1,4-dioxa-2-azonia-3-boratacyclohexane are orthorhombic, a = 7.0332(6), b = 9.2269(6), c = 22.967(2) Å, Z = 4, space group P212121. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.051 and Rw = 0.047 for 1247 reflections with 1 ≥ 2σ(I). The molecule exhibits the longest N—B and the shortest O—B distances (1.723(6) and 1.468(5) Å, respectively, corrected for libration) yet reported for a six-membered N,O-chelate of diphenylboron. Keywords: crystal structure, boron compound, organoboron compound.

Structural studies of organoboron compounds. XXXV. 4,8-Diethyl-2,2,6,6-tetraphenyl-1,3,5,7-tetraoxa-4,8-diazonia- 2,6-diborata-1,2,3,5,6,7-hexahydronaphthalene

1989 ◽  
Vol 67 (10) ◽  
pp. 1644-1649 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Mahmood Tajerbashi ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Least Squares ◽  
Title Compound ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Boron Compound ◽  
Structural Studies ◽  
Full Matrix ◽  
Binding Strength ◽  
The Mean

The reaction of Ν,Ν′-diethyloxalohydroxamic acid with oxybis(diphenylborane) yields the title compound. Crystals of 4,8-diethyl-2,2,6,6-tetraphenyl-1,3,5,7-tetraoxa-4,8-diazonia-2,6-diborata-1,2,3,5,6,7-hexahydronaphthalene are monoclinic, a = 14.3405(9), b = 14.3053(5), c = 14.9301(8) Å, β = 116.136(4)°, Z = 4, space groupP21/n. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.038 and Rw = 0.038 for 3501 reflections with I ≥ 3σ(I). The molecule has a novel bis-six-membered binuclear chelate structure, the Ph2B moieties each being coordinated by (N)O and (C=)O oxygen atoms from different hydroxamate groups. The mean libration-corrected bond distances (C=)O—B, 1.587 Å, (N)O—B, 1.511 Å, and B—C, 1.602 Å, represent the weakest overall binding strength of an O,O-chelating ligand with respect to the Ph2B moiety yet observed for a six-membered O—B—O chelate. Keywords: crystal structure, boron compound, organoboron compound.

Structural studies of organoboron compounds. XXXIX.1 1,4-Bis(2,2-diethoxyethyl)-6,8-diphenyl-5,7,9-trioxa-4-aza-1-azonia-8- bora-6-boratabicyclo[4.3.0]nonane

1990 ◽  
Vol 68 (10) ◽  
pp. 1791-1796 ◽  
Author(s):  
Henning Amt ◽  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Least Squares ◽  
Title Compound ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Structural Studies ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths

Reaction of N,N′-1,2-ethanediylidenebis(2,2-diethoxyethanamine)- N,N′-dioxide and phenylboronic acid yields the title compound. Crystals of 1,4-bis(2,2-diethoxyethyl)-6,8-diphenyl-5,7,9-trioxa-4-aza-1-azonia-8-bora-6-boratabicyclo[4.3.0]-nonane are triclinic, a = 12.625(2), b = 13.962(2), c = 9.273(1) Å, α = 104.81(1), β = 98.61(1), γ = 106.52(1)°, Z = 2, space group [Formula: see text]. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.058 and Rw = 0.081 for 3677 reflections with I ≥ 3σ(I). The molecule has a bicyclo[4.3.0]nonane structure containing one transannular N—B bond. Important bond lengths are sp3-bomn, N—B = 1.759(3), O—B = 1.435(3) and 1.454(3), C—B = 1.579(4); sp2-boron, O—B = 1.335(3) and 1.404(3), C—B = 1.557(4) Å. The (sp3)B—C(phenyl) bond is the shortest yet reported for this type of compound.Keywords: crystal structure, boron compound, organoboron compound.

Structural studies of organoboron compounds. XXIX. 6,6-Diethyl-2,2-diphenyl-1,3-dioxa-6-azonia-2-boratacyclooctane monohydrate

1988 ◽  
Vol 66 (5) ◽  
pp. 1091-1096 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Least Squares ◽  
Title Compound ◽  
Chelate Ring ◽  
Direct Methods ◽  
Structural Studies ◽  
Organoboron Compounds ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths ◽  
Conformation Intermediate

Details of the preparation and structure of the title compound are given. Crystals of 6,6-diethyl-2,2-diphenvl-1,3-dioxa-6-azonia-2-boratacyclooctane monohydrate are orthorhombic, a = 7.0322(2), b = 16.3505(7), c = 16.8164(4) Å, Z = 4, space group P212121. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.045 and Rw = 0.050 for 2013 reflections with I ≥ 3σ(I). The monocyclic eight-membered B, N-betaine is the first to be structurally characterized. The eight-membered chelate ring has a conformation intermediate between the S4 and boat-boat forms which is probably stabilized by transannular [Formula: see text] interactions. The average libration-corrected O—B and B—C bond lengths of 1.500 and 1.639 Å are, respectively, the shortest and longest yet observed for an O,O-chelate of diphenylboron.

Structural studies of organoboron compounds. XXX. 1,9-Dimethyl-3,5,7-triphenyl-2,4,6,8-tetraoxa-1,9-diazonia-5-bora-3,7- diboratatricyclo[5.4.0.03,9]undecane

1988 ◽  
Vol 66 (5) ◽  
pp. 1117-1122 ◽  
Author(s):  
Henning Amt ◽  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Physical Properties ◽  
Least Squares ◽  
Title Compound ◽  
Direct Methods ◽  
Ring System ◽  
Structural Studies ◽  
Organoboron Compounds ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths

Details of the preparation and physical properties of the title compound are given. Crystals of 1,9-dimethyl-3,5,7- triphenyl-2,4,6,8-tetraoxa-1,9-diazonia-5-bora-3,7-diboratatricyclo[5.4.0.03,9]undecane are orthorhombic, a = 9.4026(3), b = 9.4663(2), c = 24.7462(9) Å, Z = 4, space group P212121. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.036 and Rw = 0.038 for 1536 reflections with I ≥ 3σ(I). The three six-membered and two seven-membered rings comprising the tricyclo[5.4.0.03,9]undecane ring system all have boat or boat-like conformations. Important bond lengths (corrected for libration) are: B(sp3)—N = 1.649(6) and 1.668(6), B(sp3)—O(N) = 1.492(5) and 1.497(6), B(sp3)—O[B(sp2)] = 1.444(6) and 1.438(5), B(sp3)—C = 1.600(6) and 1.594(7), B(sp2)—O = 1.357(6) and 1.370(6), B(sp2)—C = 1.574(6) Å.

Structural studies of organoboron compounds. XXXVII. 8,8-Pentamethylene-6-phenyl-6,9-epoxy-5,7-dioxa-8-azonia-6-borata-6,7,8,9-tetrahydro-5H-benzocycloheptene

1990 ◽  
Vol 68 (1) ◽  
pp. 64-68 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Hans-Walter Motzkus ◽  
Klaus Drückler ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Least Squares ◽  
Title Compound ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Structural Studies ◽  
Boron Compounds ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths

Condensation of equimolar amounts of salicylaldehyde, N-hydroxypiperidine, and phenylboronic acid yields the title compound. Crystals of 8,8-pentamethylene-6-phenyl-6,9-epoxy-5,7-dioxa-8-azonia-6-borata-6,7,8,9-tetrahydro-5H-benzocycloheptene are monoclinic, a = 12.773(1), b = 11.9600(7), c = 10.6411(6) Å, β = 103.786(7)°, Z = 4, space group P21/c. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.039 and Rw = 0.047 for 2420 reflections with I ≥ 3σ(I). The compound has a bridged heterocyclic B,N-betaine structure with a PhB(OR)3 anionic centre. Bond lengths (corrected for libration) include: B—O(aryl C) = 1.481(2), B—O(alkyl C) = 1.488(2), B—O(N) = 1.539(2), and B—C = 1.591(2) Å. Keywords: organoboron, boron compounds, crystal structure.

Structural studies of organoboron compounds. XX.(Salicylaldoximato-O,N)diphenylboron

1984 ◽  
Vol 62 (7) ◽  
pp. 1363-1368 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Hydrogen Bonds ◽  
Least Squares ◽  
Chelate Ring ◽  
Direct Methods ◽  
Structural Studies ◽  
Organoboron Compounds ◽  
Full Matrix ◽  
Space Group ◽  
Bond Lengths ◽  
Phenolic Oxygen

Crystals of (salicylaldoximato-O,N)diphenylboron are triclinic, a = 10.125(2), b = 10.797(1), c = 14.760(2) Å, α = 89.05(1), β = 86.98(1), γ = 83.18(1)°, Z = 4, space group [Formula: see text]. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.040 and Rw = 0.048 for4145 reflections with I ≥ 3σ(I). The structure consists of two crystallographically independent, but essentially identical, molecules linked by strong [Formula: see text] hydrogen bonds to form continuous spirals along the a axis. The Ph2B moiety is chelated by the phenolic oxygen and oxime nitrogen atoms of the ligand resulting in the formation of a non-planar six-membered chelate ring. Important libration-corrected mean bond lengths are O—B = 1.516(1), N—B = 1.609(2), and C—B = 1.613(2) Å.

Structural studies of organoboron compounds. XLIII. 4-[(1-Hydroxycyclohexyl)methyl]-2,2,5-triphenyl-1,3-dioxa-4-azonia-2-borata-4-cyclopentene

1991 ◽  
Vol 69 (3) ◽  
pp. 545-549 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Ute Schumacher ◽  
Mahmood Tajerbashi ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Least Squares ◽  
Key Words ◽  
Hydroxamic Acid ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Structural Studies ◽  
Full Matrix ◽  
Bond Lengths ◽  
Acid Chelate

The reaction of N′-hydroxy-N-[(1-hydroxycyclohexyl)methyl]benzamide and diphenylborinic anhydride gives 4-[(1-hydroxycyclohexyl)methyl]-2,2,5-triphenyl-1,3-dioxa-4-azonia-2-borata-4-cyclopentene in nearly quantitative yield. Crystals of the product are monoclinic, a = 9.9117(6), b = 13.308(1), c = 17.339(2) Ǻ, β = 99.420(7)°, Z = 4, space group P21/c. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.040 and Rw = 0.047 for 2423 reflections with I > 3σ(I). The molecule has a normal five-membered hydroxamic acid chelate structure, the BONCO ring having a B-envelope conformation. Bond lengths (corrected for libration) (N)O—B = 1.535(3), (C)O—B = 1.569(3), C—B = 1.603(3) and 1.601(3) Ǻ are normal for this type of complex. Key words: organoboron compound, boron compound, crystal structure.

Structural studies of organoboron compounds. XLII. 4,6-Bis(1-cyano-1-methylethyl)-2-mesityl-1,3-dioxa-4,6-diaza-2-boracyclohexane

1991 ◽  
Vol 69 (2) ◽  
pp. 234-238 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Gottfried Lubkowitz ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Least Squares ◽  
Key Words ◽  
Good Yield ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Structural Studies ◽  
Full Matrix ◽  
Bond Lengths

The condensation of N,N′-bis(1-cyano-1-methylethyl)-N,N′-dihydroxymethanediamine and mesitylboronic acid gives 4,6-bis(1-cyano-1-methylethyl)-2-mesityl-1,3-dioxa-4,6-diaza-2-boracyclohexane in good yield. Crystals of the latter compound are orthorhombic, a = 15.825(1), b = 17.958(1), c = 14.014(1) Ǻ, Z = 8, space group Pbca. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.037 and Rw = 0.051 for 2844 reflections with 1 ≥ 3σ(I). The molecule has a six-membered cycloboronate structure featuring the first structurally characterized BONCNO ring. The ring was found to have a C-envelope conformation in the solid state. Bond lengths include: O—B(sp2) = 1.356(2) and 1.370(2), and C(aryl)—B = 1.560(2) Ǻ. Key words: organoboron compound, boron compound, crystal structure.

Structural studies of organoboron compounds. XXXVIII. 2,2-Diphenyl-4,4-tetramethylene-1,3,5-trioxa-3a-azonia-2-borata-2,3,4,5-tetrahydro-1H-cyclopenta[a]naphthalene

1990 ◽  
Vol 68 (1) ◽  
pp. 69-73 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Mahmood Tajerbashi ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Title Compound ◽  
Good Yield ◽  
Chelate Ring ◽  
Condensation Product ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Structural Studies ◽  
Weakly Bound ◽  
Full Matrix

Reaction of oxybis(diphenylborane) with the condensation product of salicylohydroxamic acid and cyclopentanone gives the title compound in good yield. Crystals of 2,2-diphenyl-4,4-tetramethylene-1,3,5-trioxa-3a-azonia-2-borata-2,3,4,5-tetrahydro-1H-cyclopenta[a]naphthalene are monoclinic, a = 12.521(1), b = 12.409(1), c = 12.975(1) Å, β = 93.784(8)°, Z = 4, space group P21/n. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.043 and Rw = 0.044 for 1502 reflections with I ≥ 2σ(I). The molecule has a typical diphenylboron hydroxamate structure featuring a five-membered COBON chelate ring. The O,O-chelating ligand is weakly bound to the diphenylboron moiety. Bond lengths (corrected for libration) include: (N)O—B = 1.558(4), (C=)O—B = 1.578(4), and C—B = 1.589(5) and 1.603(5) Å. Keywords: crystal structure, boron compound, organoboron compound.

Structural studies of organoboron compounds. XV. Crystal and molecular structures of (3-aminopropanolato)diphenylboron, (2-N,N-dimethylaminoethanolato)diphenylboron, and (2-N,N-dimethylaminoethanolato)diphenylboron – diphenylborinic acid (1:1)

1983 ◽  
Vol 61 (10) ◽  
pp. 2334-2340 ◽  
Author(s):  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Least Squares ◽  
Boron Atom ◽  
Direct Methods ◽  
Molecular Structures ◽  
Structural Studies ◽  
Organoboron Compounds ◽  
Full Matrix ◽  
Space Group ◽  
Crystal And Molecular Structures

Crystals of (3-aminopropanolato)diphenylboron are monoclinic, a = 9.6717(13). b = 9.8867(6), c = 14.452(2) Å, β = 99.500(7)°, Z = 4, space group P21/n: those of (2-N,N-dimethylaminoethanolato)diphenylboron are monoclinic, a = 7.0721(4), b = 16.8829(4), c = 12.0975(8) Å, β = 97.875(3)°, Z = 4, space group Cc; and those of (2-N,N-dimethylaminoethanolato)diphenylboron – diphenylborinic acid (1:1) are monoclinic. a = 11.3231(10). b = 19.3190(12). c = 12.2451(11) Å, β = 109.321(4)°, Z = 4, space group P21/n. All three structures were solved by direct methods and were refined by full-matrix least-squares procedures to final R values of 0.038. 0.031, and 0.040 for 1522, 1649, and 2420 reflections with I ≥ 3σ(I) respectively. Each structure contains a tetrahedrally coordinated boron atom. The libration-corrected B—O, B—N, and mean B—C distances are: 1.481(2), 1.643(3), and 1.623(3) Å for (3-aminopropanolato)diphenylboron; 1.476(2), 1.691 (2), and 1.625(7) Å for (2-N,N-dimethylaminoethanolato)diphenylboron. The Ph2BOH molecule contains a trigonal-planar boron atom with B—O = 1.354(3) Å and mean B—C = 1.572(3) Å.

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