Complexes of Bis(chlorodimethylstannyl)- and Bis(dichloromethylstannyl)methanes with Aromatic Nitrogen Heterocycles

Martin Austin; Kassu Gebreyes; Henry G. Kuivila; Kamal Swami; Jon A. Zubieta

doi:10.1021/om00147a024

Complexes of Bis(chlorodimethylstannyl)- and Bis(dichloromethylstannyl)methanes with Aromatic Nitrogen Heterocycles

Martin Austin, Kassu Gebreyes, Henry G. Kuivila, Kamal Swami, Jon A. Zubieta

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Abstract

The preparations and structures determined by X-ray diffraction of the following complexes of bis-(chlorodimethylstannyl)methane and bis(dichloromethylstannyl)methane with aromatic nitrogen heterocycles are described: CH₂(ClMe₂Sn)₂.C₅H₅N (U (C₅H₄N = pyridine); CH₂(ClMe₂Sn)₂-C₄H₄N₂(2) (C₄H₄N₂= pyridazine); CH₂(Cl₂MeSn)₂-2C₄H₄N₂(3) (C₄H₄N₂= pyridazine); CH₂(ClMe₂Sn)₂' 2C₃H₄N₂(4) (C₃H₄N₂= pyrazole); CH₂(ClMe₂Sn)₂-C₄H₄N₂(5) (C₄H₄N₂= pyrazine); CH₂(Cl₂MeSn)₂*C₄H₄N₂(6) (C₄H₄N₂= pyrazine); CH₂(Cl₂MeSn)₂*bpy (7) (bpy = bipyridyl). Crystal data are as follows. 1: triclinic P1, a-7.192 (2) Å, b = 10.175 (2) Å, c = 12.853 (3) Å, a = 111.76 (1)°, S = 95.09 (1)°, 7 = 105.40 (1)°, V = 823.5 (8) Å¹^{2 3}⁴, D(calcd) = 1.86 g cm^-3for Z-2; R = 0.037 for 1691 reflections. 2: monoclinic PS^/n, a = 9.330 (2) Å, b = 17.224 (3) Å, c = 9.860 (2) Å, fi = 97.78 (1)°, V = 1569.9 (9) Å³, D(calcd) = 1.96 g cm^-3for Z = 4; R = 0.036 for 1865 reflections. 3: orthorhombic Pnam, a = 8.758 (2) Å, b = 13.111 (3) Å, c = 16.366 (3) Å, V-1879.2 (9) Å³, D(calcd) = 2.06 g cm^-3for Z = 4; R-0.026 for 815 reflections. 4: orthorhombic P2₁2₁2₁, a = 10.178 (2) Å, b = 10.365 (2) Å, c = 17.670 (3) Å, V = 1864.0 (8) Å³, D(calcd) = 1.84 g cm^-3for Z = 4; R = 0.046 for 1195 reflections. 5: triclinic P1, a = 6.939 (2) Å, b = 9.624 (2) Å, c = 10.460 (2) Å, a = 102.21 (1)°, 0 = 92.38 (1)°, 7 = 90.39 (1)°, D(calcd) = 2.03 g cm^-3for Z = 1; R = 0.026 for 1518 reflections. 6: orthorhombic space group Pbnb, a = 9.964 (2) Å, b = 12.414 (3) Å, c = 12.510 (3) Å, V = 1547.3 (9) Å³, D(calcd) = 2.04 g cm^-3for Z = 4; R = 0.022 for 860 reflections. 7: monoclinic P2i/n, a = 12.845 (3) Å, b = 11.617 (2) Å, c = 15.361 (3) Å, (3 = 95.45 (1)°, 7 = 2281.8 (10) A³, D(calcd) = 1.69 g cm^-3for Z = 4; R = 0.051 for 1344 reflections. The X-Sn-Y distances for both trigonal-bipyramidal and octahedral structures at tin fit the bond order correlation functions of Britton and Dunitz for S_N2 and S_N3 reaction pathways.

Original language	English (US)
Pages (from-to)	834-842
Number of pages	9
Journal	Organometallics
Volume	6
Issue number	4
DOIs	https://doi.org/10.1021/om00147a024
State	Published - Apr 1 1987
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om00147a024

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@article{cbe02b16088841878ca71bc73231d71d,

title = "Complexes of Bis(chlorodimethylstannyl)- and Bis(dichloromethylstannyl)methanes with Aromatic Nitrogen Heterocycles",

abstract = "The preparations and structures determined by X-ray diffraction of the following complexes of bis-(chlorodimethylstannyl)methane and bis(dichloromethylstannyl)methane with aromatic nitrogen heterocycles are described: CH2(ClMe2Sn)2.C5H5N (U (C5H4N = pyridine); CH2(ClMe2Sn)2-C4H4N2(2) (C4H4N2= pyridazine); CH2(Cl2MeSn)2-2C4H4N2(3) (C4H4N2= pyridazine); CH2(ClMe2Sn)2' 2C3H4N2(4) (C3H4N2= pyrazole); CH2(ClMe2Sn)2-C4H4N2(5) (C4H4N2= pyrazine); CH2(Cl2MeSn)2*C4H4N2(6) (C4H4N2= pyrazine); CH2(Cl2MeSn)2*bpy (7) (bpy = bipyridyl). Crystal data are as follows. 1: triclinic P1, a-7.192 (2) {\AA}, b = 10.175 (2) {\AA}, c = 12.853 (3) {\AA}, a = 111.76 (1)°, S = 95.09 (1)°, 7 = 105.40 (1)°, V = 823.5 (8) {\AA}12 34, D(calcd) = 1.86 g cm-3for Z-2; R = 0.037 for 1691 reflections. 2: monoclinic PS^/n, a = 9.330 (2) {\AA}, b = 17.224 (3) {\AA}, c = 9.860 (2) {\AA}, fi = 97.78 (1)°, V = 1569.9 (9) {\AA}3, D(calcd) = 1.96 g cm-3for Z = 4; R = 0.036 for 1865 reflections. 3: orthorhombic Pnam, a = 8.758 (2) {\AA}, b = 13.111 (3) {\AA}, c = 16.366 (3) {\AA}, V-1879.2 (9) {\AA}3, D(calcd) = 2.06 g cm-3for Z = 4; R-0.026 for 815 reflections. 4: orthorhombic P212121, a = 10.178 (2) {\AA}, b = 10.365 (2) {\AA}, c = 17.670 (3) {\AA}, V = 1864.0 (8) {\AA}3, D(calcd) = 1.84 g cm-3for Z = 4; R = 0.046 for 1195 reflections. 5: triclinic P1, a = 6.939 (2) {\AA}, b = 9.624 (2) {\AA}, c = 10.460 (2) {\AA}, a = 102.21 (1)°, 0 = 92.38 (1)°, 7 = 90.39 (1)°, D(calcd) = 2.03 g cm-3for Z = 1; R = 0.026 for 1518 reflections. 6: orthorhombic space group Pbnb, a = 9.964 (2) {\AA}, b = 12.414 (3) {\AA}, c = 12.510 (3) {\AA}, V = 1547.3 (9) {\AA}3, D(calcd) = 2.04 g cm-3for Z = 4; R = 0.022 for 860 reflections. 7: monoclinic P2i/n, a = 12.845 (3) {\AA}, b = 11.617 (2) {\AA}, c = 15.361 (3) {\AA}, (3 = 95.45 (1)°, 7 = 2281.8 (10) A3, D(calcd) = 1.69 g cm-3for Z = 4; R = 0.051 for 1344 reflections. The X-Sn-Y distances for both trigonal-bipyramidal and octahedral structures at tin fit the bond order correlation functions of Britton and Dunitz for SN2 and SN3 reaction pathways.",

author = "Martin Austin and Kassu Gebreyes and Kuivila, {Henry G.} and Kamal Swami and Zubieta, {Jon A.}",

year = "1987",

month = apr,

day = "1",

doi = "10.1021/om00147a024",

language = "English (US)",

volume = "6",

pages = "834--842",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Complexes of Bis(chlorodimethylstannyl)- and Bis(dichloromethylstannyl)methanes with Aromatic Nitrogen Heterocycles

AU - Austin, Martin

AU - Gebreyes, Kassu

AU - Kuivila, Henry G.

AU - Swami, Kamal

AU - Zubieta, Jon A.

PY - 1987/4/1

Y1 - 1987/4/1

N2 - The preparations and structures determined by X-ray diffraction of the following complexes of bis-(chlorodimethylstannyl)methane and bis(dichloromethylstannyl)methane with aromatic nitrogen heterocycles are described: CH2(ClMe2Sn)2.C5H5N (U (C5H4N = pyridine); CH2(ClMe2Sn)2-C4H4N2(2) (C4H4N2= pyridazine); CH2(Cl2MeSn)2-2C4H4N2(3) (C4H4N2= pyridazine); CH2(ClMe2Sn)2' 2C3H4N2(4) (C3H4N2= pyrazole); CH2(ClMe2Sn)2-C4H4N2(5) (C4H4N2= pyrazine); CH2(Cl2MeSn)2*C4H4N2(6) (C4H4N2= pyrazine); CH2(Cl2MeSn)2*bpy (7) (bpy = bipyridyl). Crystal data are as follows. 1: triclinic P1, a-7.192 (2) Å, b = 10.175 (2) Å, c = 12.853 (3) Å, a = 111.76 (1)°, S = 95.09 (1)°, 7 = 105.40 (1)°, V = 823.5 (8) Å12 34, D(calcd) = 1.86 g cm-3for Z-2; R = 0.037 for 1691 reflections. 2: monoclinic PS^/n, a = 9.330 (2) Å, b = 17.224 (3) Å, c = 9.860 (2) Å, fi = 97.78 (1)°, V = 1569.9 (9) Å3, D(calcd) = 1.96 g cm-3for Z = 4; R = 0.036 for 1865 reflections. 3: orthorhombic Pnam, a = 8.758 (2) Å, b = 13.111 (3) Å, c = 16.366 (3) Å, V-1879.2 (9) Å3, D(calcd) = 2.06 g cm-3for Z = 4; R-0.026 for 815 reflections. 4: orthorhombic P212121, a = 10.178 (2) Å, b = 10.365 (2) Å, c = 17.670 (3) Å, V = 1864.0 (8) Å3, D(calcd) = 1.84 g cm-3for Z = 4; R = 0.046 for 1195 reflections. 5: triclinic P1, a = 6.939 (2) Å, b = 9.624 (2) Å, c = 10.460 (2) Å, a = 102.21 (1)°, 0 = 92.38 (1)°, 7 = 90.39 (1)°, D(calcd) = 2.03 g cm-3for Z = 1; R = 0.026 for 1518 reflections. 6: orthorhombic space group Pbnb, a = 9.964 (2) Å, b = 12.414 (3) Å, c = 12.510 (3) Å, V = 1547.3 (9) Å3, D(calcd) = 2.04 g cm-3for Z = 4; R = 0.022 for 860 reflections. 7: monoclinic P2i/n, a = 12.845 (3) Å, b = 11.617 (2) Å, c = 15.361 (3) Å, (3 = 95.45 (1)°, 7 = 2281.8 (10) A3, D(calcd) = 1.69 g cm-3for Z = 4; R = 0.051 for 1344 reflections. The X-Sn-Y distances for both trigonal-bipyramidal and octahedral structures at tin fit the bond order correlation functions of Britton and Dunitz for SN2 and SN3 reaction pathways.

AB - The preparations and structures determined by X-ray diffraction of the following complexes of bis-(chlorodimethylstannyl)methane and bis(dichloromethylstannyl)methane with aromatic nitrogen heterocycles are described: CH2(ClMe2Sn)2.C5H5N (U (C5H4N = pyridine); CH2(ClMe2Sn)2-C4H4N2(2) (C4H4N2= pyridazine); CH2(Cl2MeSn)2-2C4H4N2(3) (C4H4N2= pyridazine); CH2(ClMe2Sn)2' 2C3H4N2(4) (C3H4N2= pyrazole); CH2(ClMe2Sn)2-C4H4N2(5) (C4H4N2= pyrazine); CH2(Cl2MeSn)2*C4H4N2(6) (C4H4N2= pyrazine); CH2(Cl2MeSn)2*bpy (7) (bpy = bipyridyl). Crystal data are as follows. 1: triclinic P1, a-7.192 (2) Å, b = 10.175 (2) Å, c = 12.853 (3) Å, a = 111.76 (1)°, S = 95.09 (1)°, 7 = 105.40 (1)°, V = 823.5 (8) Å12 34, D(calcd) = 1.86 g cm-3for Z-2; R = 0.037 for 1691 reflections. 2: monoclinic PS^/n, a = 9.330 (2) Å, b = 17.224 (3) Å, c = 9.860 (2) Å, fi = 97.78 (1)°, V = 1569.9 (9) Å3, D(calcd) = 1.96 g cm-3for Z = 4; R = 0.036 for 1865 reflections. 3: orthorhombic Pnam, a = 8.758 (2) Å, b = 13.111 (3) Å, c = 16.366 (3) Å, V-1879.2 (9) Å3, D(calcd) = 2.06 g cm-3for Z = 4; R-0.026 for 815 reflections. 4: orthorhombic P212121, a = 10.178 (2) Å, b = 10.365 (2) Å, c = 17.670 (3) Å, V = 1864.0 (8) Å3, D(calcd) = 1.84 g cm-3for Z = 4; R = 0.046 for 1195 reflections. 5: triclinic P1, a = 6.939 (2) Å, b = 9.624 (2) Å, c = 10.460 (2) Å, a = 102.21 (1)°, 0 = 92.38 (1)°, 7 = 90.39 (1)°, D(calcd) = 2.03 g cm-3for Z = 1; R = 0.026 for 1518 reflections. 6: orthorhombic space group Pbnb, a = 9.964 (2) Å, b = 12.414 (3) Å, c = 12.510 (3) Å, V = 1547.3 (9) Å3, D(calcd) = 2.04 g cm-3for Z = 4; R = 0.022 for 860 reflections. 7: monoclinic P2i/n, a = 12.845 (3) Å, b = 11.617 (2) Å, c = 15.361 (3) Å, (3 = 95.45 (1)°, 7 = 2281.8 (10) A3, D(calcd) = 1.69 g cm-3for Z = 4; R = 0.051 for 1344 reflections. The X-Sn-Y distances for both trigonal-bipyramidal and octahedral structures at tin fit the bond order correlation functions of Britton and Dunitz for SN2 and SN3 reaction pathways.

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UR - http://www.scopus.com/inward/citedby.url?scp=0001098682&partnerID=8YFLogxK

U2 - 10.1021/om00147a024

DO - 10.1021/om00147a024

M3 - Article

AN - SCOPUS:0001098682

SN - 0276-7333

VL - 6

SP - 834

EP - 842

JO - Organometallics

JF - Organometallics

IS - 4

ER -

Complexes of Bis(chlorodimethylstannyl)- and Bis(dichloromethylstannyl)methanes with Aromatic Nitrogen Heterocycles

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