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Are there compounds that have the same SMILES code but are not stereoisomers?

User Bacher
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Final answer:

The SMILES code system is designed to uniquely represent the structure of molecules, including their stereochemistry. While omitting stereochemical details can mean a SMILES code represents multiple isomers, generally, a unique SMILES code refers to a singular chemical species, making non-isomeric compounds with identical SMILES highly unlikely.

Step-by-step explanation:

The student asked if there are compounds that have the same SMILES code but are not stereoisomers. To address this question, it is essential to understand what isomers are. Isomers are compounds with the same molecular formula but different arrangements of atoms in space. They could have the same sequence of bonds (as in constitutional isomers) or different spatial arrangements (as in stereoisomers).

Regarding SMILES (Simplified Molecular Input Line Entry System), it's a notation system that describes a chemical structure using short ASCII strings. SMILES can specify stereochemistry, however, if stereochemical details are omitted, the SMILES code may represent more than one isomer, including stereoisomers.

But fundamentally, a valid SMILES code should not represent non-isomeric compounds since the sequence of atoms and their connectivity are defined. The precise structural representation includes chiral centers and double bond geometries to distinguish between different isomers.

Another important aspect to consider is that compounds with the same molecular formula may still be isomers even if they don't differ in their stereochemistry. For example, butane C4H10 exists as two isomers: n-butane and isobutane. They have different physical properties, such as boiling points, and different structures, but the same molecular formula.

Regarding the case of acetic acid, C2H4O2, additional isomers like methyl formate have the same molecular formula but different atom-to-atom bonding and structural arrangements, showing that compounds can indeed be isomeric without being stereoisomers.

User Nakhodkin
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