lewis acid chemistry of some sulphur-nitrogen compounds · lewis.acid chemistry of some...
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LEWIS.ACID CHEMISTRY OF SOME SULPHUR-NITROGEN' COMPOUNDS
By
JOHN DAYIa TYRER, B.Se.
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,A The's i s
SUbmi tted to the Sqhoo'l of Graduate Studi es
in Partial Ful fi lment of t'h~ Requireme'nts.for" the Degre\,..\_•...:. ,', ' .
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Doctor of Ph'Hosophy,"
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McMaster Uhiversity
. ~ePte'!lber, 1978
'©. J.D, Tyrer, '1~78,
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LEWIS ACID CHEMISTRY OF SOME SULPHUR-NITROGEN COMPOUNDS.
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TO MY PAREIHS
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DOCTOR OF PHILOSOPHY(Chemistry) .
..
McMaster Un~versityHamil ton, On~ario
v' TITLE: Lewis ACi, Chemistry of Some Sulphur-Nitrogen Compounds~ .
AUTHOR: Tyrer, ~.Sc. (McMa~ter u.niversityf
.sUPERV ISOR: or R.J . Gill espi e
:..~UMBER OF PAGES: . xvi, 203 .jI~ -
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ABSTRACT
The compound S4N4 has been shown to react with the Lewis acids
SbC1S' SbFS and AsFSto produce the previously unreported cyclotetra,-. 2' I
thiazyl dication, S4N4f, in the form of the salts S4N4(SbC16)2~ S4N4(SbF6)2'
, S4N4(AsF6)2'~S02' and S4 N4(Sbl14
)(SbF6)· A re.action sequenci~for the pre
p'aration of S4N4(SbC16)2 has been sugges.ted and the infrared and'Raman_\..
spectra for, each of the salts is reported as w'ell as the crystal struc,.
,tures of the' S4N4,(SbC16)2 and S4N4.(:bl14)(Sb~6) salts',
A brief investigation ~f th~ r~action of S4N4 with. the Lewis
acids PFS. afld PC1 S p~oduced; i.n the Si-l4/PFS ,system, the ne\'I ~olecu-lar
adduct, S~N4 ,PFS': ~/hereas the reaction of S.4N4 wH~ PC1 S yLe1'dec(a"
complex mixture of products, composed of phosphonittilic chlorides",
The chemistry of trichlorocycl~trithia~ene~ith SbC1 S h?~ beenI
studied, ,It has been d~termined for the first time ,that S31'l3C13 when
oxidized'lby SbC1 S p'roduces the S4N4(SbC16)2 salt ~lith the co"!pounds
S4N4'SbC1S and SS~5(SbC16) isolated ai inter~ediates forme~ during'
the pr~duction of the S4'N~+, dicatio~, The crystal struct~res of 'both
S4tl4,SbCls and SSN S(SbC1 6) are reported i':l this th.esis'~, , • It
'In contrast, t~e fluoride, trifluorocyclotr~thiaz~ne,S3N3F3', . .
whe~ combin~d with the Lewis acids ,SbFS' AsfS .and S03 was no~ oxidlzed
but rather simple fluoride ion abstraction occurred t~yield the thialyl
salts SN (SbzF11), SN (As F6})and SN ('sal) ,For the f.irst time, the chemistry of the sulphur imides witb. "
Le~'1i s aci ds of oxi dati ve capab'i 1i ty has been s tudi ed,
Cyclotetrasulphurtetraimide, S4N4H4i ~e~cted readily with
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S4,N 4(S?CJ6)2, Trye 'compo~nd,s4nd'SbC1S
a~.'intertnediate armed du'rirtg the oxfdation ofSbCl q. to yi ehi. the
S4N4H4 with SbC1 S'. . "..' '.. .. .,
. Cyc 1, ohe'p t-asu 1phuri mi de, . S7'N:H, and 1',4.-.cyc 1ohexasu 1[)h ur.di i mi de',
1,4-S6NZH2 , produced the pre'ViOus1Y:"u.nkn~\'/~ '~,ithion~'troni-tJnJ 'ion, 'S2N+,:,
when treate~'w;tn' SbC1S
' . Infrared ~nd Raman-spectra i 9r the S2N(SbC15}.' , "T '"
are reported as well as'the crystal st,ructu:re.T. ;, 4 •
In a limited,investigation, th~ co.mpo~nq CllNPC13{PC16h has .,'• < • ,
been isolat'~d from the':eaction, of S7N~ W.i,th ,PelS.' !he cr~s,tal-st,~~c-:, ,
" ,
ttl re 0 f the': tri.ch 1orp[ ( tri eh lora phos phora ny1idene )amim ] phosphorus (V)
hexach 1orophos pha teo is reported in tfl i s wbrk. ., .
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ACKNOlolLEDGEMEilTS
The author vlishes to express his sincere appreci at i on to
·all those ~ho contributed towards this thesis, in oarticular:
'To the 1ate Dr. F:P. 01 sen for his encouragement and gui dance
during the initial stages of this project;
,To Professor R.J, Gill~spie for his aid'and supervision
during the course of this work, and for the helpful discussions in
the prepara~~on of this thesis;
To pro D.R. Slim for the X-ray structural analyses of the.'
compounds S4N4(SbC16)2' S4N4(Sb3F14)(SbF6)' S4N4'SbC1 S and SSNS(SbC~6);
To Dr. C.J.L. Lock and Mr. R. Faggiani for the X-ray struc-
, tural determin~ti"On of S2N(SbC1 6);
To Dr. J. Sa\'tyer for the X-ray structural determination of
(C1 3PNPC1 3)(PC1 6);
To Mrs. Jan Gallo for her patience and care in typing this
thesis;
To Miss N.J. Railton for her care in doing many of the illus-
trations in this thesis;"'
'To Mr.' F. Ramelan for preparing .the spti!ctra for use in this
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TABLE OF CONTENTS
Pdge
ABSTRACT 'J i 1 i>,
ACKNOWLEDGEMENTS vI
TABLE OF CONTENTS vi
LIST .OF FIGURES"
LIST OF TABLES
.CHAPTER I - INTRODUCnON
1-1 . TheChem;stry of' S4N4
1-2 ·Reactions of S4N4
, (i) I{ith Lewis 'Bases
(ii) ~ith Lewis Acids
1-3 Trich1orocyc1otrithiazene.1-4 Trifluorbcyc1otrithiazene
1-5 The Chemistry of the Sulphur Imides
Cyc10heptasulphurimide
(i) Ring Cleavage
(ii) Addition Reactions
I' Cyc1ote'trasu1 phurtett'aimide
, 3
3
8
11
20
22
24
26
27.1-6 Bonding in Cyclic Su1'phur Nitrides (N'eutral., Anionic,
and Cationic Species)
1-7 Aims of the Present Work
I
30
31
~HAPTER II - PREPARATION AND PURIFICATION OF STARTING MATERIALS 32
11-1 Preparation of S4N4
11-2 Preparation of S4N4H4
I 1-3 Prepara tion 0 f S7NH
vi
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33
34
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11-4 Preparation of S7NCH3
11-5 Preparatio.n of S3N3C13It
11-6 Preparation of S3N/3
11-7 Preparation and PurIfication of MaterialsI
11-8 General Experimental T~chniques
11-9 Instrumentation
35
35
36
38
39
41
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(i)
(i i)
(i i i)
( ; v) ~
(v)
(vi)
_( vii)
Infrared Sp~c troscopy
Raman Spectroscopy
Electron Spin Resonance Spectroscopy
Nuclear Magnetic Resohance Spectroscopy(a) 19F NMR Spectra
(b) 31 p NMR Spectra
Mass Spectroscopy
Dry Box
Ana 1ys es.
41
41
42
~2
42
43
43
43
43
CHAPTER III - LEWIS ACID CHEMISTRY OF S4N4
111-1 Reaction of S4N4 with Lewis ACIds
111-2 The PC1 S/S4N4 and PF S/S4N4 Systems
111-3 Raman and Infrared Spectra of the Molecular Adducts
of S4N4
44
44
44
52
111-4 The ReactIon of S4N4 with Anhydrous HF 58
. 111-5 The Reaction of S4~4 with WF 6 in a 1:3 Mole RatIO 60
111-9 . Structure of the Cyclotetrathldzyl Oicatlon
111-10 The Sb3F~4 Anion
,I
I I 1-6
I I 1- 7
I 11-8
The S4N4/SbC16 System
The S4N4/AsFS and S4N4/SbFS Systems2+Infrared and Raman Spectra of S4N4 Sa 1ty' t>
61
66
69
81
92
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II 1-11
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Exper1menta 1 SE>C t Ion
The ReactIon of <; 1N, '0'/ i th a Ld r'le £xcec;" of SbCJ~• "t
The Reac t ion of S4N4 \'Ji th SbC 1 r. 1n d 1:3 Mole)
Rd t 10
The Reaction of S4 N4'SbC1 S with SbCl S 1n J 1: Z
Mo Ie Ru t 10
The ReactIon 9~4N4 wIth SbCl~ In a 1:2 MoleRa t 10
The ReactIOn of S4N4 with PF S In d 1:3 Mole
Ratio
92
94
9b
The Reaction of S4N4 wI th 'Anhydro'Js Hi=" In LiqUId S02
The Reaction of S4N4 .wi th WF ti 1n J 1,.:3 ~'ole RJt10..., . \
The-ReactIon of S4N4 wIth AsFS
In 1:3 and 1:6
~lo1e Ratios
) CHAPTER IV
IV-I
IV -2
IV - 3
IV -4\.
IV - S
IV -6
'"The Reaction of S4~4 with One Mole of PC1S in
CH2C1
2
The Reaction of S4N4 wi-th SbFS
In a J-:4 Ho Je RatIO
The ReactIon of S4N-l wi th 5bFS
ih (l 1 : 3 Mo 1e Rat 10
The Reaction of 54 N4 wi th Anhydrous HF
- THE LEI.JIS ACID CHEMISTRY OF S3N/13 and SIN/ 3
Reactions of S3Nl13 and S3N/3vWlth LeWIS t'\cld.,
The S3N3C13/SbC15 System
The S3N3F3/Lewi" ACId System
Mass Speclra of S3N/3 and S3~13C13
The Crystal Structure of SSN S(SbC16
)
The Crystal Structure of S4N4'SbCIS
vii i
97
98
99
, 100
100
101~
102
103
103
103
115-1') ')
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124
130
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CHAPTER Vf - 'SUMMARY~ CONCltJS fONS.I •
V1-1 lo~cJ~? lons/;'- '/ t,
VI-2 SuggeStions for Future Work
Page
185
185 .
190
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BIBL IOGRAPHY.... '
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V-4 The Infrared and Raman Sp~ctra of (S2N)(SbC16)
v-s The Crystal 'Structure of S2N(SbC16)I
V-6 The S7NH/PC1S System
V-7 The Crystal Structure of (Cl 1P-N-PC1;)(PC1;)
V-8 Experimental Section
(,
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V-3 +The Dithionitronium Ion, S2N
Page
150
157
160
163
169
176
The Reaction of Heptasulfurimide with SbC1 S in a1:2 Mole Ratio 176
'\
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J
The Reaction of Heptasulphurimide with BC13
andSbC1 S
The Reaction .of 1,4-S6N2H2 with SbC1 S in a 1:4Mole Ratio
The Reaction of S4N4H4 with SbC1 S in a 1:3 MoleRatio
..IiThe R~action of S4N4H4 with SbC1 S in a 1:5 MoleRatio
The Reaction of S7NCH3 with SbC1 S in a 1:3 MoleRatio
177
178
179 .
179
180
( ,
The Reaction of S7NH with AsFS in a 1:3 Mole Ratio 181
The Reaction of S7NH with SbFS in a 1:3 Mole Ratio 181
The Reaction.of S7NCH3 with AsFS in a 1:10 MoleRatio '"18'2
The ~eaction of S7NH with PC1 S in a 1:2 Mole Ratio 182
The Reaction,of'S7NH with PFS in a 1:2 Mole Ratio 183
The Reacti~n of S7NCH3,with PFS in a 1:2 Mole Ratio 184
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Page
IV-7 Bonding in. Su1phur- Nitrogen Ring Systems
IV-8 Experimental Section
The Reaction of S3N3C13 wit~ SbC15
in Liquid SO'2in a 1:2 Mole Ratio
The Reaction of S3N3C13 with SbC1 S in SOC1 2in a 1:2 Mole Ratio
The Reaction of S3N3C13 wi th SbC1 S in a 1: 2Mo 1e Ratio
1. The Reaction of S3N3Cl3 with SbC1 S in CH ZC1 Z ina1: 1 Mole Ra ti 0. \
\i~: The Reaction of S3N3C13 wi th SbC1 S in S02 in a 1:1It
Mole Ratio~
140
140
14D
141
142
142
143
r-'\
'Preparation of S3N3C1'2(SbC'6) from the Reaction of
S3N3C13 with SbC1 S in CC1 4 in a 1:1 Mole Ratio
Solutions of S3N3C12(SbC16) in CH 2C'2 and S?2
Preparati on of. (SsNS)(SbC1 6 ) by the Method of
Banister
144
144
144
:.
The Reaction of S3Nl3 with S03 in a 1:3 Mole Ratio' 145
The ,~eaction of S3Nl3 with SbFS in a 1:6 Mole Ratio 146
The Reaction of S3N3F3 with SbFS in a ':2 Mole Ratio 146
The Reaction of S3N3F3 with AsF5 in a 1:6 Mole Ratio 146
The R~action of S3N3F3 with A~FS and SbFS in a 1:2Mole Ratio 147
CHAPTER V - 'THE ..,lEWIS ACID CHEMISTRY OF THE SULPHUR IMIDES 148
.,-{
V-1 Reactions of the Sulphur Imides with Lewis Acids
ix
148
148
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LIST OF FIGURES
Figure Page
1-1
II -1
II-2
II 1-1
I JI-2
I II-3
111-4
1II-5
4- "The S4N4 Anion
Double Bul.b Reaction Vessel
Single Bulb Reaction Vessel with nmr Tube
31 p nmr spectra of (a) S4N4 with PCl S in a 1:1 molar
ratio, (b) S4N4 with PC1 S in a 1:3 molar rati~ ,19 '
Room temperature F nmr spectrum of "the S4N4,PFSadduct
Room temperature 31 p nmr spectrum of the S4N4·PFSadduct
First-order stick diagram illustrating the 31~ nmr
spectrum of the S4N4'PF5 adduct
Infrared spectra of the S4~'SbC1S and S4N4'PFSmolecular adducts
29
40
40
45
50
51
., 51
54
II 1-6 Raman spectrum of the S4N4'SbC1S adduct recorded at- 196 O'C
111-7 Proposed st~ucture of the S4N4SbC1: intermediate
I~I-8 Infrared spectra of S4N4(SbC'6)2 and· S4N4(A~F6)2'XS02
111-9 Infrared spectra of S4N4(SbF6)2 and S4N4(Sb3F,4)(SbF6)
111-10 Raman spectrum of S4N4~SbC16)2 recorqed at -196°C
111-11 Raman spectrum of S4N4(AsF6)Z"xSOZ re.corded at -196°C
~11-12 Raman spectrum of S4N4~bF6)Z recorded at -196°C
111-13 R~man spectrum of S4N4(~b3F14)(Sb~6) recorded at -t96°C
111-14 Unit cell diagram of S4N4(SbC16)z
111-15 Unit cell diagram of ~~N4(Sb3~14)(SbF6)
'IlI-16 (A) Structure of ring (A) in [S4N4][SbF6]ESbl14]"
(B) Structure of ring (B) in [S4N4][SbF6][Sb3F14]
xii
55
65
71
72
73
74
75
76
82
83
89
89
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89
89
90
Page
(C)
(C')
(
,>,Structure of ring (C) in [S4N4][SbC16J2 vieweddown the 54 axis
J. I
Structure of ring, (C) ~;ewed down the pseudo-C2axi s
111-17 Valence bond diagrams of the,s4N~+ cation
Fi gure
III-18 The Sbl14 anion, --- long contacts to neighbouringF atoms 91
IV -1
IV-2
IV-3
IV-4
IV-S
IV-6
IV-7
IV-8
IV-9
Raman spectru~ recorded at -196°C of the greenmaterial isolated from the reac'tion of S3N3Ci~ith '.SbC1 S in a 1:2 molar ratio in liquid S02
Raman spectrum of SN(S03F) recorded at -196°C
Raman spectrum a! SN(AsF6) .and other.uni~e~tified
products recorded at -196°C
Raman spectrum of SN(SbZF11 ) recorded at -196°C+ .
The SSNS ca tl on
The unit ce~l di~gram of SSNS(SbC1 6).The unit cell ~diagram of 'S4.N( SbC1 S
The mo)ecular ~uct S4N4'SbC1S
Valence Bon9 Resonance Forms for' the Molecular Adduct
S4N~'SbCls
106
117
118
119
125·
lZ6
131
132
133~
IV-10. Variation of S-N-S Bond Angle with S-N Bond Distance 138~
IV-ll Variation of N-S-N S'ond Angle with S-N Bond Distance 139'
h
, "
"
V-1
V-2
V-3
Proposed Reaction Sequence for the Oxidation of S7NH~nd l,4-Si N2H2 with SbC1 S
Raman spectrum of S2N(S~C16) recorded at -196°C. .The unit cell diagram of S2N(SbC16), a and bare.pa'rallel to the top and side of the page. res pec1\vel y ,
and the view is down c.
153
159
162
xi i i, .
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