Impact of Cyclometalation and π-Conjugation on Photoisomerization of an N,C-Chelate Organoboron Compound

2011 ◽  
Vol 30 (16) ◽  
pp. 4453-4458 ◽  
Author(s):  
Ying-Li Rao ◽  
Suning Wang
Keyword(s):  
Organoboron Compound

Highly emissive B←N unit containing four-coordinate C,N-Chelated organoboron compound for the detection of fluoride ions

2019 ◽  
Vol 166 ◽  
pp. 410-415 ◽  
Author(s):  
Ni Yan ◽  
Fengyan Wang ◽  
Junji Wei ◽  
Jiale Song ◽  
Luke Yan ◽  
...  
Keyword(s):  
Organoboron Compound ◽  
Fluoride Ions

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. 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. 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.

Novel boron chelate complexes from the reaction of salicylaldehydes, tertiary amines, and diphenylborinic or phenylboronic acid. Crystal and molecular structures of two new types of chelated organoborate salts

1997 ◽  
Vol 75 (9) ◽  
pp. 1203-1214 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Jörg Metge ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Tertiary Amine ◽  
Phenylboronic Acid ◽  
Reaction System ◽  
Organoboron Compound ◽  
Ammonium Cation ◽  
Acid Anhydride ◽  
Molecular Structures ◽  
One Pot ◽  
Space Group ◽  
Three Component Reaction

The one-pot reaction of equimolar amounts of salicylaldehyde, diphenylborinic acid anhydride, and a tertiary amine in the presence of an alkanol (R′OH) led to the addition of R′OH to the aldehyde group and the formation of an O,O-acetal moiety within the chelate anion with the charge balanced by an ammonium cation arising from the tertiary amine. Exchanging the diphenylborinic acid in the three-component reaction system for phenylboronic acid did not give the analogous adduct or chelate but one additional mole equivalent of phenylboronic acid (anhydride) was incorporated, leading to a polycyclic anion containing pyroboronate and acetal boronate functions with an associated ammonium cation. Crystals of 1-methylpiperidinium 4-ethoxy-2,2-diphenyl-1,3-dioxa-2-borata-1,2,3,4-tetrahydronaphthalenate, 6d, are monoclinic, a = 9.522(1), b = 17.703(1), c = 14.974(1) Å, β = 98.275(10)°, Z = 4, space group P21/n, and those of 1-methylpiperidinium 6,10-epoxy-4-methoxy-6,8-diphenyl-5,7,9-trioxa-8-bora-6-borata-5,6,7,8,9,10-hexahydrobenzocyclooctenate, 10e, are monoclinic, a = 7.968(1), b = 19.3707(4), c = 15.9400(5) Å, β = 100.186(5)°, Z = 4, space group P21/n, The structures were solved by direct methods and refined by full-matrix least-squares procedures to R = 0.050 and 0.033 (Rw = 0.040 and 0.032) for 2815 and 3529 reflections with I ≥ 3σ(F2), respectively. Compounds 6d and 10e are both representative of new classes of organoboron chelates. Keywords: salicylaldehyde semiacetal diphenylboron chelate, salicylaldehyde bisboronate, organoboron compound, crystal structure.

AMINOETHYL DIARYLBORINATES; ISOLATION OF A STABLE UNSYMMETRICAL ORGANOBORON COMPOUND

1954 ◽  
Vol 76 (15) ◽  
pp. 4047-4048 ◽  
Author(s):  
Robert L. Letsinger ◽  
Ivan Skoog ◽  
Nathaniel Remes
Keyword(s):  
Organoboron Compound

Structural studies of organoboron compounds XLVIII. 1,4-Diphenyl-3,3:6,6-bis(tetramethylene)-2,5,7-trioxa-3,6-diazonia-1,4-diboratabicyclo[2.2.1]heptane

1991 ◽  
Vol 69 (8) ◽  
pp. 1222-1226 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Ulf Riebe ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Phenylboronic Acid ◽  
Direct Methods ◽  
Organoboron Compound ◽  
Ring System ◽  
Structural Studies ◽  
Full Matrix ◽  
Moderate Yield ◽  
Atom Bond ◽  
Axis Passing

The reaction of N-hydroxypyrrolidine with either oxybis(diphenylborane) or phenylboronic acid gives 1,4-diphenyl-3,3:6,6-bis(tetramethylene)-2,5,7-trioxa-3,6-diazonia-1,4-diboratabicyclo[2.2.1]heptane in moderate yield. Crystals of the product are orthorhombic, a = 10.984(2), b = 14.619(2), c = 12.311(2) Å, Z = 4, space group Pccn. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.039 and Rw = 0.043 for 908 reflections with I ≥ 3σ(I). This is the first heterocyclic [2.2.1]heptane system containing a six-membered BONBON ring and a B—O—B bridge to be structurally characterized. The molecule has exact C2 symmetry with the twofold axis passing through the bridging oxygen atom. Bond lengths involving the tetrahedrally coordinated boron atom are B—O(B) = 1.423(3), B—O(N) = 1.497(3), B—N = 1.703(3), and B—C(phenyl) = 1.577(4) Å. Key words: 2,5,7-trioxa-3,6-diazonia-1,4-diboratabicyclo[2.2.1]heptane ring system, crystal structure, organoboron compound.

Structural studies of organoboron compounds. XLIV. 2,3-Dihydro-3-hydroxy-2,2-tetramethylene-4H-benzoxazin-4-one and its difluoroboron chelate, 2,2-difluoro-4,4-tetramethylene-1,3,5-trioxa-3a-azonia-2-borata-2,3,4,5-tetrahydro- 1H-cyclopenta[a]naphthalene

1991 ◽  
Vol 69 (4) ◽  
pp. 673-680 ◽  
Author(s):  
Wolfgang Kliegel ◽  
Mahmood Tajerbashi ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Crystal Structure ◽  
Boron Trifluoride ◽  
Chelate Ring ◽  
Direct Methods ◽  
Organoboron Compound ◽  
High Yield ◽  
Structural Studies ◽  
Crystal Forms ◽  
Full Matrix ◽  
Weak Binding

The reaction of 2,3-dihydro-3-hydroxy-2,2-tetramethylene-4H-benzoxazin-4-one, 2, and diethyl ether–boron trifluoride yields the difluoroboron chelate 2,2-difluoro-4,4-tetramethylene-1,3,5-trioxa-3a-azonia-2-borata-2,3,4,5-tetrahydro- 1H-cyclo-penta[a]naphthalene, 6, in high yield. There are two crystal forms of 2: 2a, triclinic, [Formula: see text] a = 8.551(1), b = 9.331(3), c = 7.236(1) Å, α = 103.38(2), β = 104.68(1), γ = 80.37(2)°, Z = 2, ρc = 1.35 g cm−3, and 2b, monoclinic, C2/c, a = 17.41(2), b = 10.665(6), c = 12.427(8) Å, β = 115.74(5)°, Z = 8, ρc = 1.40 g cm−3. Crystals of 6 are monoclinic, P21/c, a = 5.354(1), b = 17.654(2), c = 12.844(1) Å, β = 100.11(2)°, Z = 4, ρc = 1.48 g cm−3. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to final R values of 0.046, 0.046, and 0.041 for 1712, 1505, and 1675 reflections with I ≥ 3σ(I), respectively. In both forms of 2, the structures consist of centrosymmetric [Formula: see text] hydrogen-bonded dimers [Formula: see text] for 2a and 2.682(3) Å for 2b). The difluoroboron chelate 6 features a five-membered chelate ring planar within 0.068(2) Å, and bond lengths O—B = 1.504(3) and 1.516(3), F—B = 1.358(3) and 1.359(3) Å indicate weak binding of the ligand to the F2B moiety. Key words: organoboron compound, crystal structure, boron compound

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