Synthesis and Characterization of New Diazenecarboxamide Ligands Using a Selective Adduct Formation with B(C6F5)3

Escobar, Manuel A.; Valderrama, Mauricio; Daniliuc, Constantin G.; Rojas, Rene S.

doi:10.5935/0103-5053.20150270

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Journal of the Brazilian Chemical Society

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Articles • J. Braz. Chem. Soc. 27 (1) • Jan 2016 • https://doi.org/10.5935/0103-5053.20150270 copy

Synthesis and Characterization of New Diazenecarboxamide Ligands Using a Selective Adduct Formation with B(C₆F₅)₃

Authorship SCIMAGO INSTITUTIONS RANKINGS

The synthesis and structure of new N-(2,6-diisopropylphenyl)-2-phenyldiazenecarboxamide (L₂) and N-(2,6-diisopropylphenyl)-2 (perfluorophenyl) diazenecarboxamide (L₃) ligands are described. The subsequent reactions of ligands L₁, L₂ and L₃ with trispentafluorophenylboron gave rise to new adducts (A₁), (A₂) and (A₃), where B(C₆F₅)₃ is coordinated to the carbonyl group. New ligands and adducts are characterized by nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis techniques. The crystal structures of all compounds are obtained and described.

Keywords:
diazenecarboxamide ligands; borane adduct; azo compounds

	L₁	L₂	L₃	A₁	A₂	A₃
NMR δ¹H / ppm
N-H	8.69	8.03	7.80	9.22	8.61	8.49
HC^iPr	-	3.19	3.16	-	2.99	2.95
Me^iPr	-	1.23	1.24	-	1.18	1.15
NMR δ¹³C / ppm
(C=O)	157.9	160.4	159.3	160.8	163.8	162.9
FTIR / cm^-1
v(C=O)	1700	1702	1693	1646	1649	1648

	L₁	L₂	L₃	A₁	A₂	A₃
Bond lengths (Å)
O(1)-C(2)	1.217(2)	1.217(3)	1.217(2)	1.260(3)	1.262(2)	1.251(4)
N(1)-C(2)	1.338(2)	1.333(3)	1.321(3)	1.308(3)	1.309(3)	1.306(5)
N(3)-C(2)	1.466(2)	1.464(3)	1.462(3)	1.423(3)	1.432(3)	1.434(5)
N(3)-N(4)	1.246(2)	1.227(3)	1.233(2)	1.249(2)	1.252(2)	1.242(4)
O(1)-B(1)	-	-	-	1.565(3)	1.577(3)	1.593(5)
Bond Angles (°)
O(1)-C(2)-N(1)	127.3(1)	126.8(2)	128.0(2)	121.7(2)	121.1(2)	121.3(3)
O(1)-C(2)-N(3)	124.4(1)	116.5(2)	118.0(2)	118.5(2)	118.8(2)	121.8(3)
O(1)-B(1)-C(41)	-	-	-	101.1(2)	111.0(2)	109.0(3)
O(1)-B(1)-C(51)	-	-	-	108.8(2)	106.0(2)	104.5(3)
O(1)-B(1)-C(61)	-	-	-	-	102.1(2)	101.9(3)
O(1)-B(1)-C(31)	-	-	-	109.3(2)	-	-

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