Is Rust's lexical grammar regular, context-fre

The lexical grammar of most programming languages is fairly non-expressive in order to quickly lex it. I'm not sure what category Rust's lexical grammar belongs to. Most of it seems regular, probably with the exception of raw string literals:

let s = r##"Hi lovely "\" and "#", welcome to Rust"##;
println!("{}", s);

Which prints:

Hi lovely "\" and "#", welcome to Rust

As we can add arbitrarily many #, it seems like it can't be regular, right? But is the grammar at least context-free? Or is there something non-context free about Rust's lexical grammar?

Related: Is Rust's syntactical grammar context-free or context-sensitive?

The raw string literal syntax is not context-free.

If you think of it as a string surrounded by r#^k"…"#^k (using the superscript k as a count operator), then you might expect it to be context-free:

raw_string_literal
   : 'r' delimited_quoted_string
delimited_quoted_string
   : quoted_string
   | '#' delimited_quoted_string '#'

But that is not actually the correct syntax, because the quoted_string is not allowed to contain "#^k although it can contain "#^j for any j<k

Excluding the terminating sequence without excluding any other similar sequence of a different length cannot be accomplished with a context-free grammar because it involves three (or more) uses of the k-repetition in a single production, and stack automata can only handle two. (The proof that the grammar is not context-free is surprisingly complicated, so I'm not going to attempt it here for lack of MathJax. The best proof I could come up with uses Ogden's lemma and the uncommonly cited (but highly useful) property that context-free grammars are closed under the application of a finite-state transducer.)

C++ raw string literals are also context-sensitive [or would be if the delimiter length were not limited, see Note 1], and pretty well all whitespace-sensitive languages (like Python and Haskell) are context-sensitive. None of these lexical analysis tasks is particularly complicated so the context-sensitivity is not a huge problem, although most standard scanner generators don't provide as much assistance as one might like. But there it is.

Rust's lexical grammar offers a couple of other complications for a scanner generator. One issue is the double meaning of ', which is used both to create character literals and to mark lifetime variables and loop labels. Apparently it is possible to determine which of these applies by considering the previously recognized token. That could be solved with a lexical scanner which is capable of generating two consecutive tokens from a single pattern, or it could be accomplished with a scannerless parser; the latter solution would be context-free but not regular. (C++'s use of ' as part of numeric literals does not cause the same problem; the C++ tokens can be recognized with regular expressions, because the ' can not be used as the first character of a numeric literal.)

Another slightly context-dependent lexical issue is that the range operator, .., takes precedence over floating point values, so that 2..3 must be lexically analysed as three tokens: 2 .. 3, rather than two floating point numbers 2. .3, which is how it would be analysed in most languages which use the maximal munch rule. Again, this might or might not be considered a deviation from regular expression tokenisation, since it depends on trailing context. But since the lookahead is at most one character, it could certainly be implemented with a DFA.

Postscript

On reflection, I am not sure that it is meaningful to ask about a "lexical grammar". Or, at least, it is ambiguous: the "lexical grammar" might refer to the combined grammar for all of the languages "tokens", or it might refer to the act of separating a sentence into tokens. The latter is really a transducer, not a parser, and suggests the question of whether the language can be tokenised with a finite-state transducer. (The answer, again, is no, because raw strings cannot be recognized by a FSA, or even a PDA.)

Recognizing individual tokens and tokenising an input stream are not necessarily equivalent. It is possible to imagine a language in which the individual tokens are all recognized by regular expressions but an input stream cannot be handled with a finite-state transducer. That will happen if there are two regular expressions T and U such that some string matching T is the longest token which is a strict prefix of an infinite set of strings in U. As a simple (and meaningless) example, take a language with tokens:

a
a*b

Both of these tokens are clearly regular, but the input stream cannot be tokenized with a finite state transducer because it must examine any sequence of as (of any length) before deciding whether to fallback to the first a or to accept the token consisting of all the as and the following b (if present).

Few languages show this pathology (and, as far as I know, Rust is not one of them), but it is technically present in some languages in which keywords are multiword phrases.

Notes

Actually, C++ raw string literals are, in a technical sense, regular (and therefore context free) because their delimiters are limited to strings of maximum length 16 drawn from an alphabet of 88 characters. That means that it is (theoretically) possible to create a regular expression consisting of 13,082,362,351,752,551,144,309,757,252,761 patterns, each matching a different possible raw string delimiter.