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The synthesis, structural characterization and biocidal properties of some triorganotin(IV) esters of N ‐arylidene‐ω‐amino acids.
Author(s) -
Goh Ngoh Khang,
Chu Chit Kay,
Khoo Lian Ee,
Whalen Deborah,
Eng George,
Smith Frank E.,
Hynes Rosemary C.
Publication year - 1998
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/(sici)1099-0739(199806)12:6<457::aid-aoc720>3.0.co;2-z
Subject(s) - chemistry , monoclinic crystal system , carboxylate , denticity , crystal structure , tributyltin , stereochemistry , tin , crystallography , organic chemistry
The methods of synthesis, elemental analysis, IR and NMR spectroscopic data and fungicidal activity against Ceratocystis ulmi are reported for a series of triorganotin esters of N ‐arylidene‐ω‐amino acids of general formula R 3 SnOCO(CH 2 ) n N = CHAr (R = Ph, n‐Bu; Ar = 2‐HOC 6 H 4 , 2‐HOC 10 H 6 ; n = 1, 2, 3 and 5). The crystal structures for two of the compounds, tributyltin N ‐2‐hydroxynaphthalidene glycinate ( 1 ) and tributyltin N ‐2‐hydroxynaphthalidene‐β‐alaninate ( 2 ), have been determined. Although both of these compounds have a trans ‐R 3 SnO 2 structure, in compound 1 the carboxylate group is monodentate and the fifth coordination position around the tin atom is taken up by a coordinated phenolic group, whereas in 2 the carboxylate group is bridging. These two examples thus correspond to the two different structures reported for trans ‐R 3 SnO 2 complexes. Both compounds were found to be active against Ceratocystis ulmi , but there was no significant difference in their levels of biological activity against this particular fungus. Apart from compound 1 , the other tributyltin compounds reported are believed to adopt the carboxylate bridging mode shown by compound ( 2 ). Crystal data: for 1 , crystals monoclinic, space group P 2 1 / c , a = 12.9435(11) Å, b = 13.5769(10) Å, c = 15.7715(12) Å, β = 108.919(6)°, Z = 4, R f = 0.046 and R w = 0.058 for 1448 significant reflections; for 2 , crystals monoclinic, space group C 2/ c , a = 24.588(14) Å, b = 9.733(3) Å, c = 27.611(12) Å, β = 113.49(4)°, Z = 8, R f = 0.053 and R w = 0.069 for 3822 significant reflections. © 1998 John Wiley & Sons, Ltd.