The Lewis structures are then evaluated based on the following set of rules: (1) The lower the sum of formal charges in a Lewis structure, the more significant the contribution of that Lewis structure to the resonance hybrid will be. (2) Lewis structures with the following features will not have high contribution to the resonance hybrid - unless they are the only possible Lewis structures for the molecule/ion: (a) positive F.C. on more electronegative atom (b) negative F.C. on an atom other than the most electronegative one (3) Consider Lewis structures with the following features only if no other structures fit: (a) an individual F.C. higher than 1 (b) two formal charges of the same sign on adjacent atoms Problem. The thiocyanate ion and isothiocyanate ion are two polyatomic anions made up of carbon (C), nitrogen (N), and sulfur (S) atoms. The scafolding of thiocyanate is (S--N--C)¹, while the scaffolding of isothiocyanate is (S--C--N). Each ion has three possible resonance structures. Despite their structural similarities, one of these ions is quite stable, while the other is highly reactive (unstable). In this problem, we will predict and explain the factors that contribute to their different stabilities. A. To begin, draw three resonance structures for each polyatomic ion. Isothiocyanate ion (S---C---N) -2 S = C=N S=C=N: . O Y S-C=N": Most stable Thiocyanate ion, (S---N---C)-¹:
The Lewis structures are then evaluated based on the following set of rules: (1) The lower the sum of formal charges in a Lewis structure, the more significant the contribution of that Lewis structure to the resonance hybrid will be. (2) Lewis structures with the following features will not have high contribution to the resonance hybrid - unless they are the only possible Lewis structures for the molecule/ion: (a) positive F.C. on more electronegative atom (b) negative F.C. on an atom other than the most electronegative one (3) Consider Lewis structures with the following features only if no other structures fit: (a) an individual F.C. higher than 1 (b) two formal charges of the same sign on adjacent atoms Problem. The thiocyanate ion and isothiocyanate ion are two polyatomic anions made up of carbon (C), nitrogen (N), and sulfur (S) atoms. The scafolding of thiocyanate is (S--N--C)¹, while the scaffolding of isothiocyanate is (S--C--N). Each ion has three possible resonance structures. Despite their structural similarities, one of these ions is quite stable, while the other is highly reactive (unstable). In this problem, we will predict and explain the factors that contribute to their different stabilities. A. To begin, draw three resonance structures for each polyatomic ion. Isothiocyanate ion (S---C---N) -2 S = C=N S=C=N: . O Y S-C=N": Most stable Thiocyanate ion, (S---N---C)-¹:
Principles of Modern Chemistry
8th Edition
ISBN:9781305079113
Author:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Publisher:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Chapter3: Atomic Shells And Classical Models Of Chemical Bonding
Section: Chapter Questions
Problem 99AP: A stable triatomic molecule can be formed that contains one atom each of nitrogen, sulfur, and...
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Transcribed Image Text:The Lewis structures are then evaluated based on the following set of rules:
(1) The lower the sum of formal charges in a Lewis structure, the more significant the
contribution of that Lewis structure to the resonance hybrid will be.
(2) Lewis structures with the following features will not have high contribution to the
resonance hybrid - unless they are the only possible Lewis structures for the molecule/ion:
(a) positive F.C. on more electronegative atom
(b) negative F.C. on an atom other than the most electronegative one
(3) Consider Lewis structures with the following features only if no other structures fit:
(a) an individual F.C. higher than 1
(b) two formal charges of the same sign on adjacent atoms
Problem. The thiocyanate ion and isothiocyanate ion are two polyatomic anions made up of
carbon (C), nitrogen (N), and sulfur (S) atoms. The scafolding of thiocyanate is (S--N--C)¹, while
the scaffolding of isothiocyanate is (S--C--N). Each ion has three possible resonance structures.
Despite their structural similarities, one of these ions is quite stable, while the other is highly
reactive (unstable). In this problem, we will predict and explain the factors that contribute to
their different stabilities.
A. To begin, draw three resonance structures for each polyatomic ion.
Isothiocyanate ion (S---C---N)
-2
S = C=N
S=C=N:
. O
Y
S-C=N":
Most stable
Thiocyanate ion, (S---N---C)-¹:
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