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How do atoms Can heteroatoms with 3 different covalently bonded substituents and one electron pair behavelone pairs be chiral centres?

If onea compound has a carbon atom with 4four different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etcof the compound can exist.  

But imagine if one has a different central atom, for examplesuch as a nitrogen or a $\ce{C^{1+}}$ sosulfur where one of the groupsfour "groups" is an electron pair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$(see examples below).

Will suchAn explosive chloramine and a sulfonium ion

Would such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I, i.e. are there enantiomers etc.? IsIs my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would alsoalso enjoy pointers to literature, I was unable to find any.

How do atoms with 3 different covalently bonded substituents and one electron pair behave?

If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.  

But imagine if one has a different central atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron pair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

Can heteroatoms with lone pairs be chiral centres?

If a compound has a carbon atom with four different groups covalently bonded to it, it is called asymmetric and enantiomers of the compound can exist.

But imagine if one has a different central atom, such as a nitrogen or a sulfur where one of the four "groups" is an electron pair (see examples below).

An explosive chloramine and a sulfonium ion

Would such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave, i.e. are there enantiomers? Is my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

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If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.

But imagine if one has a different central atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron pair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

Thanks for your time

If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.

But imagine if one has a different central atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron pair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

Thanks for your time

If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.

But imagine if one has a different central atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron pair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

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How do atoms with 3 different covalently bonded thingssubstituents and one filled electron cloudpair behave?

If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.

But imagine if one has a different central atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron cloudpair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have sp3$\mathrm{sp^3}$ hybrid orbitals wrong? I I would also enjoy pointers to literature, I was unable to find any.

Thanks for your time

How do atoms with 3 different covalently bonded things and one filled electron cloud behave?

If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.

But imagine one has a different atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron cloud. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have sp3 hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

Thanks for your time

How do atoms with 3 different covalently bonded substituents and one electron pair behave?

If one has a carbon atom with 4 different groups covalently bonded to it, it is called asymmetric and there can be enantiomers etc.

But imagine if one has a different central atom, for example a nitrogen or a $\ce{C^{1+}}$ so one of the groups is an electron pair. E.g. $\ce{NR_{1}R_{2}R_{3}}$ ; $\ce{NHClBr}$

Will such a thing still behave like a "normal" asymmetric carbon? If not, how else does it behave? I.e. are there enantiomers etc.? Is my assumption that those will still have $\mathrm{sp^3}$ hybrid orbitals wrong? I would also enjoy pointers to literature, I was unable to find any.

Thanks for your time

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